Herbicidal compositions

ABSTRACT

The present invention relates to a herbicidal composition comprising 
 
A) one or more compounds of the formula (I)  
                 
         where V is an unsubstituted or substituted heterocyclyl radical or a radical —CR α ═CR β  R β1 , where R α  and R β  are identical or different carbon-containing C 1 -C 40  radicals which together can form an unsubstituted or substituted ring, and R β1   is OH or a carbon-containing C 1 -C 40  radical, and Z is an unsubstituted or substituted aryl radical, and B) one or more surfactants comprising, as structural element, at least 10, alkylene oxide units.

The invention is in the technical field of the crop protection products,in particular, the invention relates to herbicidal compositions with acontent of particular herbicidal compounds and specific surfactantswhich are outstandingly suitable for controlling harmful plants incrops.

Some of the more recent herbicidal active ingredients which inhibitp-hydroxyphenyl-pyruvate dioxygenase (HPPDO) show very good propertieson use and can be employed in very low rates of application against abroad spectrum of graminaceous and broad-leaved weeds (see, for example,Prisbylla et al., Brighton Crop Protection Conference—Weeds (1993),731-738).

U.S. Pat. No. 5,627,131 and EP 551650 disclose specific mixtures ofherbicides with pre-emergence safeners.

It is furthermore known from various publications that herbicides fromthe series of the benzoylcyclohexanediones, being inhibitors ofpara-hydroxyphenyl-pyruvate dioxygenase, are based on the same mechanismof action as those from the series of the benzoylisoxazoles; in thiscontext cf. J. Pesticide Sci. 21, 473-478 (1996); Weed Science 45,601-609 (1997), Pesticide Science 50, 83-84, (1997) and PesticideOutlook, 29-32, (December 1996). Moreover, it is known from PesticideScience 50, 83-84, (1997) that, under certain conditions,benzoylisoxazoles can undergo rearrangements to givebenzoyl-3-oxopropionitriles.

It is likewise known that the abovementioned herbicidal compounds can becombined with surfactants to produce standard formulations.

Thus, for example, WO 98/31223 describes the use of mixtures comprisinga fatty acid ester or an alkoxy fatty acid, a terpene derivative and apesticide. EP-A 0 968 649 describes dry formulations of herbicidescomprising ethoxylated fatty alcohols. The herbicide-comprising mixturesmentioned therein do not always exhibit the desired potent herbicidalaction.

The object of the present invention was to provide herbicidalcompositions which have a particularly potent herbicidal action.

Surprisingly, it has now been found that herbicidal compositionscomprising the compounds of the formula (I) stated hereinbelow incombination with specific surfactants achieve this object.

Thus, the present invention relates to herbicidal compositionscomprising

-   A) one or more compounds of the formula (I)    -   where V is an unsubstituted or substituted heterocyclyl radical        or a radical —CR^(α)═CR^(β) R^(β1), where R^(α) and R^(β) are        identical or different carbon-containing C₁-C₄₀ radicals which        together can form an unsubstituted or substituted ring, and        R^(β1) is OH or a carbon-containing C₁-C₄₀ radical, and Z is an        unsubstituted or substituted aryl radical, and-   B) one or more surfactants comprising, as structural element, at    least 10, preferably 10-200, alkylene oxide units.

Surfactant B) preferably contains 10-150 alkylene oxide units, one ormore carbon-containing C₁-C₄₀ radicals and, if appropriate, one or morepolar functional groups. The term alkylene oxide units is preferablyunderstood as meaning units of C₂-C₁₀-alkylene oxides, such as ethyleneoxide, propylene oxide, butylene oxide or hexylene oxide, it beingpossible for the units within the surfactant to be identical ordifferent from each other.

Suitable polar functional groups include anionic groups such ascarboxylate, carbonate, sulfate, sulfonate, phosphate or phosphonate,cationic groups such as groups with a cationic nitrogen atom, forexample a pyridinium group or an —NR^(y) ₃-group, where R^(y) radicalsare identical or different and are H or an unsubstituted or substitutedC₁-C₁₀-hydrocarbon radical such as C₁-C₁₀-alkyl, electrically neutral,polar groups such as carbonyl, imine, cyano or sulfonyl, or betainicgroups such as

where m=1, 2, 3, 4 or 5 and R^(x) are identical or different and areunsubstituted or substituted C₁-C₁₀-hydrocarbon radicals such asC₁-C₁₀-alkyl.

Preferably, the composition according to the invention comprises, ascomponent B), one or more surfactants of the general formula (II)R^(y)-(EO)_(x) (PO)_(y) (EO)_(z)-R^(δ)  (II)where

-   EO denotes an ethylene oxide unit,-   PO denotes a propylene oxide unit,-   x denotes an integer from 1 to 50,-   y denotes an integer from 0 to 50,-   z denotes an integer from 0 to 50,    where the total (x+y+z)≧10 and ≦150, and-   R⁶⁵ denotes OH, an unsubstituted or substituted    C₁-C₄₀-hydrocarbonoxy radical, an O-acyl radical such as O—COR^(I),    O—CO—OR^(I), O—CO—NR^(I)R^(II), O—P(O)(R^(I))[(EO)_(u)(OR^(II))] or    O—P(O)[(EO)_(u)(OR^(I))][(EO)_(v)(OR^(II))] or NR^(I)R^(II) or    [NR^(I)R^(II)R^(III)]^(⊕)X^(⊖), where R^(I), R^(II) and R^(III) are    identical or different and denote H or an unsubstituted or    substituted C₁-C₃₀-hydrocarbon radical which can optionally be bound    via a group (EO)_(w), where w is an integer from 1 to 50, X^(⊖) is    an anion (for example the anion of an organic acid such as a    carboxylic acid anion, for example acetate or lactate, or the anion    of an inorganic acid such as ½ sulfate, [O—SO₃—CH₃]^(⊖), sulfonate,    ⅓ phosphate, phosphonate or halide such as Cl^(⊖) or Be^(⊖)), and u,    v independently of one another denote an integer from 0 to 50, and-   R^(δ) denotes H, an unsubstituted or substituted C₁-C₄₀-hydrocarbon    radical, an acyl radical such as COR^(I), CO—OR^(I),    CO—NR^(I)R^(II), P(O)(R^(I))[(EO)_(u) (OR^(II))] or    P(O)[(EO)_(u)(OR^(I))][(EO)_(v)(OR^(II))] or NR^(I)R^(II) or    [NR^(I)R^(II)R^(III)]^(⊕)X^(⊖), where R^(I), R^(II) and R^(III) are    identical or different and denote H or an unsubstituted or    substituted C₁-C₃₀-hydrocarbon radical which can optionally be bound    via a group (EO)_(w), where w is an integer from 1 to 50, X^(⊖) is    an anion (for example the anion of an organic acid such as a    carboxylic acid anion, for example acetate or lactate, or the anion    of an inorganic acid such as ½ sulfate, [O—SO₃—CH₃]^(⊖), sulfonate,    ⅓ phosphate, phosphonate or halide such as Cl^(⊖) or Br^(⊖)), and u,    v independently of one another denote an integer from 0 to 50.

The abbreviation EO in formula (II) denotes an ethylene oxide unit, alsowhen used in the definition of R^(γ) and R^(δ).

Preferred surfactants of the formula (II) are those where the total(x+y+z)≧10 and ≦150, preferably 11-100, especially preferably 12-80, and

-   R^(γ) denotes OH, an unsubstituted or substituted    C₁-C₃₀-hydrocarbonoxy radical, preferably a C₄-C₂₀-hydrocarbonoxy    radical, such as a C₈-, C₁₀-, C₁₂-, C₁₃-(for example    isotridecyl),C₁₄-, C₁₆—, C₁₈-, C₂₀-alkoxy radical, -alkenyloxy    radical or -alkynyloxy radical, or an unsubstituted or substituted    C₆₋₀C₄-aryloxy radical, for example a C₆-C₁₄-aryloxy radical which    is monosubstituted or polysubstituted by C₁-C₂₀-alkyl, such as    p-octylphenoxy, p-nonylphenoxy, 2,4-dibutylphenoxy,    2,4,6-tri-isobutylphenoxy, 2,4,6-tri-n-butylphenoxy or    2,4,6-tri-sec-butylphenoxy, or R^(γ) denotes O—CO—R^(I), O—COOR^(I),    NR^(I)R^(II) or [NR^(I) R^(II)R^(III)]^(⊕)X^(⊖), where R^(I), R^(II)    and R^(III) are identical or different or denote H, an unsubstituted    or substituted C₁-C₃₀-hydrocarbon radical, preferably a    C₄-C₂₀-hydrocarbon radical, such as a C₈-, C₁₀-, C₁₂-, C₁₃-(for    example isotridecyl), C₁₄-, C₁₆-, C₁₈-, C₂₀-alkyl radical, -alkenyl    radical or -alkynyl radical, or an unsubstituted or substituted    C₆-C₁₄-aryl radical, for example a C₆-C₁₄-aryl radical which is    mono- or polysubstituted by C₁-C₂₀-alkyl such as p-octylphenyl,    p-nonylphenyl, 2,4-dibutylphenyl, 2,4,6-tri-isobutylphenyl,    2,4,6-tri-n-butylphenyl or 2,4,6-tri-sec-butylphenyl, or R^(I),    R^(II) and R^(III) are identical or different and are    (EO)_(w)-R^(IV), where R^(IV) is H or an unsubstituted or    substituted C₁-C₂₀-hydrocarbon radical, such as a C₈-, C₁₀-, C₁₂-,    C₁₃-(for example isotridecyl), C₁₄-, C₁₆-, C₁₈-, C₂₀-alkyl radical,    -alkenyl radical or -alkynyl radical, or a C₆-C₁₄-aryl radical which    is mono- or polysubstituted by C₁-C₂₀-alkyl such as p-octylphenyl,    p-nonylphenyl, 2,4-dibutylphenyl, 2,4,6-tri-isobutylphenyl,    2,4,6-tri-n-butylphenyl or 2,4,6-tri-sec-butylphenyl and w is an    integer from 1 to 50, and X^(⊖) is an anion, and-   R^(δ) denotes H, an unsubstituted or substituted C₁-C₃₀-hydrocarbon    radical, preferably a C₁-C₂₀-hydrocarbon radical, such as a C₁-,    C₂-, C₃-, C₄-, C₅-, C₆-, C₈-, C₁₀-, C₁₂-, C₁₃-(for example    isotridecyl), C₁₄-, C₁₆-, C₁₈-, C₂₀-alkyl radical, -alkenyl radical    or -alkynyl radical, or an unsubstituted or substituted C₆-C₁₄-aryl    radical, for example a C₆-C₁₄-aryl radical which is mono- or    polysubstituted by C₁-C₂₀-alkyl, such as p-octylphenyl,    p-nonylphenyl, 2,4-dibutylphenyl, 2,4,6-tri-isobutylphenyl,    2,4,6-tri-n-butylphenyl or 2,4,6-tri-sec-butylphenyl, or R^(δ)    denotes CO—R^(I), COOR^(I), NR^(I) R^(II) or [NR^(I) R^(II) R^(III)    ]^(⊕)X^(⊖), where R^(I), R^(II) and R^(III) are identical or    different and denote H, an unsubstituted or substituted    C₁-C₃₀-hydrocarbon radical, preferably a C₁-C₂₀-hydrocarbon radical,    such as a C₁-, C₂-, C₃-, C₄-, C₅-, C₆-, C₈-, C₁₀-, C₁₂-, C₁₃-(for    example isotridecyl), C₁₄-, C₁₆-, C₁₈-, C₂₀-alkyl radical, -alkenyl    radical or -alkynyl radical, or an unsubstituted or substituted    C₆-C₁₄-aryl radical, for example a C₆-C₁₄-aryl radical which is    mono- or polysubstituted by C₁-C₂₀-alkyl, such as p-octylphenyl,    p-nonylphenyl, 2,4-dibutylphenyl, 2,4,6-tri-isobutylphenyl,    2,4,6-tri-n-butylphenyl or 2,4,6-tri-sec-butylphenyl, or R^(I),    R^(II) and R^(III) are identical or different and are    (EO)_(w)-R^(IV), where R^(IV) is H or an unsubstituted or    substituted C₁-C₃₀-hydrocarbon radical, preferably a    C₁-C₂₀-hydrocarbon radical, such as a C₁-, C₂-, C₃-, C₄-, C₅-, C₆-,    C₈-, C₁₀-, C₁₂-, C₁₃-(for example is C₁₆-, C₁₈-, C₂₀-alkyl radical,    -alkenyl radical or -alkynyl radical, or a C₆-C₁₄-aryl radical which    is unsubstituted or substituted, for example mono- or    polysubstituted by C₁-C₂₀-alkyl, such as p-octylphenyl,    p-nonylphenyl, 2,4-dibutylphenyl, 2,4,6-tri-isobutylphenyl,    2,4,6-tri-n-butylphenyl or 2,4,6-tri-sec-butylphenyl and w is an    integer from 1 to 50, and X^(⊖) is an anion.

Especially preferred surfactants of the formula (II) are those where thetotal (x+y+z) equals 11-80, preferably 12-50,

-   R^(γ) is (C₈-C₁₈)-alkoxy, (C₈-C₁₈)-alkenyloxy or (C₈-C₁₈)alkynyloxy,    (C₇-C₁₇)-alkylcarbonyloxy, (C₇-C₁₇)-alkenylcarbonyloxy,    (C₇-C₁₇)-alkynylcarbonyloxy, or (C₁-C₁₀)-alkylphenoxy such as    octylphenoxy, p-nonylphenoxy, 2,4,6-tri-n-butylphenoxy,    2,4,6-triisobutylphenoxy or 2,4,6-tri-sec-butylphenoxy, and-   R^(δ) is H, (C₁-C₁₈)-, preferably (C₁-C₆)-alkyl, (C₂-C₁₈)-,    preferably (C₂-C₆)-alkenyl or (C₂-C₁₈)-, preferably (C₂-C₆)-alkynyl,    CO—H, CO—(C₁-C₁₇)-alkyl, CO—(C₂-C₁₇)-alkenyl or CO—(C₂-C₁₇)-alkynyl.

Surfactants B), for example those of the formula (II), are known fromthe literature, for example from McCutcheon's, Emulsifiers & Detergents1994, Vol. 1: North American Edition and Vol. 2, International Edition;McCutcheon Division, Glen Rock N.J., USA and from “Surfactants inConsumer Products”, J. Falbe, Springer-Verlag Berlin, 1987. Thesurfactans B) stated herein are incorporated into this description byreference. Moreover, surfactants B), for example those of the formula(II), are also commercially available, for example under the trade namesGenapol® X or O or T series, Sapogenat® T series, Arkopal® N series,Afilan® PTU, Hordaphos® and Emulsogen® series by Clariant AG; Agrilan®types by Akcros Organics; Alkamul® and Antarox® types by Rhodia; Emulan®types (NP, OC, OG, OK) by BASF AG; Dehydol® types by Henkel; Agent W®types by Stepan Company; Crodamel® types by Croda GmbH. The surfactantsB) mentioned in the product leaflets in question are incorporated intothis description by reference.

Examples of surfactants B), for example those of the formula (II) arestated in Table 1 hereinbelow: TABLE 1 Ex. No. R^(γ) x y z R^(δ)  1octyl-O— 10 — — H  2 ″ 12 — — H  3 ″ 15 — — H  4 decyl-O— 10 — — H  5 ″15 — —  6 ″ 20 — — H  7 tridecyl-O— 10 — — H  8 ″ 11 — — H  9 ″ 12 — — H 10 ″ 13 — — H  11 ″ 14 — — H  12 ″ 15 — — H  13 ″ 16 — — H  14 ″ 17 — —H  15 ″ 18 — — H  16 ″ 19 — — H  17 ″ 20 — — H  18 ″ 25 — — H  19 ″ 30 —— H  20 ″ 15 — — Me  21 ″ 17 — — Me  22 ″ 15 — — COCH₃  23 ″ 17 — —COCH₃  24 (C₁₂-alkyl)-O— 10 — — H  25 ″ 11 — — H  26 ″ 12 — — H  27 ″ 13— — H  28 ″ 14 — — H  29 ″ 15 — — H  30 ″ 16 — — H  31 (C₁₂-alkyl)-O— 17— — H  32 ″ 20 — — H  33 ″ 15 — — Me  34 ″ 15 — — COCH₃  35(C₁₄-alkyl)-O— 10 — — H  36 ″ 11 — — H  37 ″ 12 — — H  38 ″ 13 — — H  39″ 14 — — H  40 ″ 15 — — H  41 ″ 16 — — H  42 ″ 17 — — H  43 ″ 18 — — H 44 ″ 19 — — H  45 ″ 20 — — H  46 ″ 25 — — H  47 ″ 30 — — H  48 ″ 40 — —H  49 (C₁₆-alkyl)-O— 10 — — H  50 ″ 15 — — H  51 ″ 20 — — H  52 ″ 40 — —H  53 (C₁₈-alkyl)-O— 15 — — H  54 ″ 20 — — H  55 (C₉-alkyl)-CO—O— 10 — —Me  56 ″ 11 — — Me  57 ″ 12 — — Me  58 ″ 13 — — Me  59 ″ 14 — — Me  60 ″15 — — Me  61 ″ 16 — — Me  62 ″ 20 — — Me  63 (C₁₀-alkyl)-CO—O— 10 — —Me  64 (C₁₀-alkyl)-CO—O— 15 — — Me  65 ″ 20 — — Me  66 (C₁₁-alkyl)-CO—O—10 — — Me  67 11 — — Me  68 ″ 12 — — Me  69 ″ 13 — — Me  70 ″ 14 — — Me 71 ″ 15 — — Me  72 ″ 16 — — Me  73 ″ 17 — — Me  74 ″ 20 — — Me  75 ″ 25— — Me  76 (C₁₂-alkyl)-CO—O— 10 — — Me  77 ″ 15 — — Me  78 ″ 20 — — Me 79 ″ 25 — — Me  80 (C₁₃-alkyl)-CO—O— 15 — — Me  81 ″ 10 — — Me  82 ″ 20— — Me  83 (C₁₅-alkyl)-CO—O— 15 — — Me  84 ″ 20 — — Me  85(C₉-alkyl)-CO—O— 10 — — (C₉-alkyl)-CO  86 ″ 15 — — ″  87 ″ 20 — +113 ″ 88 (C₁₁-alkyl)-CO—O— 10 — — (C₁₁-alkyl)-CO  89 ″ 15 — — ″  90 ″ 20 — —″  91 ″ 30 — — ″  92 (C₁₂-alkyl)-CO—O— 10 — — (C₁₂-alkyl)-CO  93 ″ 15 —— ″  94 ″ 20 — — ″  95 (C₁₃-alkyl)-CO—O— 10 — — (C₁₃-alkyl)-CO  96 ″ 20— — ″  97 (C₁₅-alkyl)-CO—O— 10 — — (C₁₅-alkyl)-CO  98 ″ 15 — — ″  99isotridecyl-O— — H 10 H 100 ″ — 2 10 H 101 ″ 10 2 — H 102 ″ 10 5 10 H103 (Genamin ®0 200, Clariant)

10 — — H 104 C₁₅H₂₉/C₁₇H₃₃—CO—O 9 2 — Me (Afilan ®PTU, Clariant) 105(Genapol ®3938, Clariant) C₁₂H₂₅/C₁₄H₂₉—O— 6 4 — H

Preferred as component A) are compounds of the formula (I)

in which

-   V is a radical selected from group (V1) to (V4),    where the symbols and indices have the following meanings:-   R is hydrogen, (C₁-C₁₀)alkoxycarbonyl, (C₁-C₁₀)haloalkoxycarbonyl,    (C₁-C₁₀)alkylsulfonyl, (C₁-C₁₀)alkylsulfinyl, (C₁-C₁₀)alkylthio,    COOH or cyano;-   R¹ is hydrogen or a (C₁-C₁₀)carbon-containing radical such as    (C₁-C₁₀)alkyl, (C₂-C₁₀)alkenyl, (C₂-C₁₀)alkynyl, (C₃-C₁₀)cycloalkyl,    (C₃-C₁₀)cycloalkenyl, (C₁-C₁₀)alkyl-(C₃-C₁₀)cycloalkyl,    (C₃-C₁₀)halocycloalkyl, (C₁-C₁₀)alkylthio-cycloalkyl,    (C₁-C₁₀)haloalkyl or (C₂-C₁₀)haloalkenyl;-   R² is hydrogen, (C₁-C₁₀)alkyl, (C₁-C₁₀)alkoxy, (C₁-C₁₀)haloalkyl,    halogen, (C₁-C₁₀)haloalkoxy, cyano or nitro;-   R³ is hydrogen or a (C₁-C₁₀)carbon-containing radical such as    (C₁-C₁₀)alkyl, (C₂-C₁₀)alkenyl, (C₂-C₁₀)alkynyl, (C₁-C₁₀)haloalkyl,    (C₁-C₁₀)alkoxy-(C₁-C₁₀)alkyl, (C₁-C₁₀)alkylcarbonyl,    (C₁-C₁₀)alkylsulfonyl, (C₁-C₁₀)haloalkylsulfonyl, unsubstituted or    substituted arylsulfonyl, unsubstituted or substituted    arylcarbonyl-(C₁-C₁₀)alkyl or unsubstituted or substituted    aryl-(C₁-C₁₀)alkyl;-   R⁴ is hydrogen or a (C₁-C₁₀)carbon-containing radical such as    (C₁-C₁₀)alkyl, (C₂-C₁₀)alkenyl, (C₂-C₁₀)alkynyl, (C₁-C₁₀)haloalkyl,    phenyl or benzyl;-   R⁵ is a (C₁-C₁₂)carbon-containing radical such as (C₁-C₁₀)alkyl,    (C₁-C₁₀)alkoxy, (C₁-C₁₀)alkoxy-(C₁-C₁₀)alkyl,    (C₁-C₁₀)dialkoxy-(C₁-C₁₀)alkyl, (C₁-C₁₀)alkylthio, halogen,    substituted or unsubstituted aryl, tetrahydropyran-4-yl,    tetrahydro-pyran-3-yl, tetrahydrothiopyran-3-yl,    1-methylthio-cyclopropyl, 2-ethylthio-propyl, or two radicals R⁵    together are (C₂-C₁₀)alkylene;-   R⁶ is hydroxyl or a (C₁-C₁₀)carbon-containing radical such as    (C₁-C₁₀)alkoxy, (C₁-C₁₀)haloalkoxy, formyloxy,    (C₁-C₁₀)alkylcarbonyloxy, (C₁-C₁₀)alkylsulfonyloxy,    (C₁-C₁₀)alkylthio, (C₁-C₁₀)haloalkylthio, unsubstituted or    substituted arylthio, unsubstituted or substituted aryloxy,    (C₁-C₁₀)alkylsulfinyl or (C₁-C₁₀)alkylsulfonyl;-   R⁷ is a (C₁-C₇)carbon-containing radical such as (C₁-C₄)alkyl,    (C₁-C₄)haloalkyl, (C₃-C₇)cycloalkyl, (C₁-C₄)alkyl-(C₃-C₇)cycloalkyl,    (C₃-C₇)halocycloalkyl;-   R⁸ is a (C₁-C₄)carbon-containing radical such as cyano,    (C₁-C₄)alkoxycarbonyl, (C₁-C₄)alkylcarbonyl, (C₁-C₄)alkylsulfonyl,    (C₁-C₄)alkylsulfinyl, (C₁-C₄) alkylthio, (C₁-C₄)alkylaminocarbonyl,    (C₁-C₄)dialkylaminocarbonyl;-   m is an integer from 0 to 6, where, if m≧2, the radicals R⁵ can be    identical or different from one another;    and Z is an unsubstituted or substituted aryl radical, preferably    selected from the group (Z1) to (Z5),    where the symbols and indices have the following meanings:-   R⁹ radicals are identical or different and are nitro, amino,    halogen, OH, SF₅ or a (C₁-C₁₀)carbon-containing radical such as    (C₁-C₁₀)alkyl, (C₂-C₁₀)alkenyl, (C₂-C₁₀)alkynyl, (C₁-C₁₀)haloalkyl,    (C₂-C₁₀)haloalkenyl, (C₂-C₁₀)haloalkynyl, (C₁-C₁₀)haloalkoxy,    (C₁-C₁₀)haloalkylthio, (C₁-C₁₀)alkoxycarbonyl,    (C₁-C₁₀)alkylsulfonyl, (C₁-C₁₀)alkylsulfinyl, (C₁-C₁₀)alkylthio,    arylsulfonyl, arylsulfinyl, arylthio, (C₁-C₁₀)alkoxy,    (C₁-C₁₀)alkoxy-(C₁-C₁₀)alkoxy, (C₁-C₁₀)-alkylthio-(C₁-C₁₀)-alkoxy,    (C₁-C₁₀)alkylcarbonyl, (C₁-C₁₀)alkylaminosulfonyl,    (C₁-C₁₀)dialkylaminosulfonyl, (C₁-C₁₀)alkylcarbamoyl,    (C₁-C₁₀)dialkylcarbamoyl, (C₁-C₁₀)alkoxy-(C₁-C₁₀)alkyl,    (C₁-C₁₀)haloalkoxy-(C₁-C₁₀)alkyl,    (C₁-C₄)alkoxy-(C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,    (C₃-C₆)-cycloalkyl-(C₁-C₄)-alkoxy, (C₃-C₆)cycloalkoxy-(C₁-C₄)-alkyl,    phenoxy, cyano, alkylamino, dialkylamino, unsubstituted or    substituted benzyl, unsubstituted or substituted heteroaryl,    unsubstituted or substituted heterocyclyl,    2-tetrahydrofuranyl-(C₁-C₄)alkoxy-(C₁-C₄)-alkyl, unsubstituted or    substituted heteroaryl-(C₁-C₁₀)alkyl or    di-(C₁-C₁₀)alkylphosphono-(C₁-C₁₀)alkyl;-   q is 0, 1, 2, 3, 4 or 5;-   R¹⁰ radicals are identical or different and are hydrogen,    (C₁-C₁₀)alkyl, halogen;-   R¹¹ radicals are identical or different and are (C₁-C₁₀)alkyl,    (C₂-C₁₀)alkenyl, (C₂-C₁₀)alkynyl, halogen, (C₁-C₁₀)haloalkyl,    (C₂-C₁₀)haloalkenyl, (C₂-C₁₀)haloalkynyl, (C₁-C₁₀)haloalkoxy,    (C₁-C₁₀)haloalkylthio, (C₁-C₁₀)alkoxycarbonyl,    (C₁-C₁₀)alkylsulfonyl, (C₁-C₁₀)haloalkylsulfonyl,    (C₁-C₁₀)alkylsulfinyl, (C₁-C₁₀)haloalkylsulfinyl, (C₁-C₁₀)alkylthio,    (C₁-C₁₀)alkoxy, (C₁-C₁₀)alkylcarbonyl, (C₁-C₁₀)alkylaminosulfonyl,    (C₁-C₁₀)dialkylamino-sulfonyl, (C₁-C₁₀)alkylcarbamoyl,    (C₁-C₁₀)dialkylcarbamoyl, (C₁-C₁₀)alkoxyalkyl, phenoxy, nitro,    cyano, aryl or di-(C₁-C₁₀)alkylphosphono-(C₁-C₁₀)alkyl;-   X¹ is O, CR¹⁵R¹⁶, CHOH, C═O, C═NO(C₁-C₁₀)alkyl;-   X² is O, S, SO, SO₂, CH₂, NH, N(C₁-C₁₀)alkyl, NSO₂(C₁-C₁₀)alkyl;-   R¹⁵, R¹⁶ radicals are identical or different and are hydrogen,    (C₁-C₁₀)alkyl, (C₁-C₁₀)alkoxy, (C₁-C₁₀)haloalkoxy,    (C₁-C₁₀)alkylthio, (C₁-C₁₀)haloalkylthio or R¹⁵ and R¹⁶ together    form one of the groups —O—(CH₂)₂—O—, —O—(CH₂)₃—O—, S—(CH₂)₂—S—,    —S—(CH₂)₃—S—, —(CH₂)₄—, —(CH₂)₅—;-   r is 0, 1, 2 or 3;-   t is 1 or 2;-   Y¹, Y² are SO₂ or CO, with the proviso that Y¹≠Y²,-   v is 1 or 2;-   U¹ together with the carbon atoms to which it is linked forms a    carbocyclic or heterocyclic ring which can be aromatic or fully or    partially saturated;-   U² is O, S, SO, SO₂, CH₂, NH, N(C₁-C₁₀)alkyl, NSO₂(C₁-C₁₀)alkyl;-   R¹² is hydrogen, (C₁-C₁₀)alkyl, (C₃-C₁₀)cycloalkyl, (C₂-C₁₀)alkenyl,    (C₂-C₁₀)alkynyl, optionally substituted phenyl, optionally    substituted benzyl, (C₁-C₁₀)acyl;-   R¹³ is an unsubstituted or substituted (C₁-C₁₀)hydrocarbon radical    such as (C₁-C₁₀)alkyl or aryl;-   u is 0, 1 or 2;-   R¹⁴ radicals are identical or different and are nitro, amino,    halogen, SF₅ or a (C₁-C₁₀)carbon-containing radical such as    (C₁-C₁₀)alkyl, (C₂-C₁₀)alkenyl, (C₂-C₁₀)alkynyl, (C₁-C₁₀)haloalkyl,    (C₂-C₁₀)haloalkenyl, (C₂-C₁₀)haloalkynyl, (C₁-C₁₀)haloalkoxy,    (C₁-C₁₀)haloalkylthio, (C₁-C₁₀)alkoxycarbonyl,    (C₁-C₁₀)alkylsulfonyl, (C₁-C₁₀)alkylsulfinyl, (C₁-C₁₀)alkylthio,    arylsulfonyl, arylsulfinyl, arylthio, (C₁-C₁₀)alkoxy,    (C₁-C₁₀)alkoxy-(C₁-C₁₀)alkoxy, (C₁-C₁₀)-alkylthio-(C₁-C₁₀)-alkoxy,    (C₁-C₁₀)alkylcarbonyl, (C₁-C₁₀)alkylaminosulfonyl,    (C₁-C₁₀)dialkylaminosulfonyl, (C₁-C₁₀)alkylcarbamoyl,    (C₁-C₁₀)dialkylcarbamoyl, (C₁-C₁₀)alkoxy-(C₁-C₁₀)alkyl,    (C₁-C₁₀)haloalkoxy-(C₁-C₁₀)alkyl, phenoxy, cyano, alkylamino,    dialkylamino, unsubstituted or substituted benzyl, unsubstituted or    substituted heteroaryl, unsubstituted or substituted heterocyclyl,    unsubstituted or substituted heteroaryl-(C₁-C₁₀)alkyl or    di-(C₁-C₁₀)alkylphosphono-(C₁-C₁₀)alkyl, and-   w is 0, 1, 2, 3 or 4.

A large number of compounds of the formula (I) which are within thescope of the invention can exist in different tautomeric structures,depending on external conditions such as solvent and pH.

Thus, for example, in the event that V=V3 and R6 hydroxyl, severaltautomeric structures are possible:

Depending on the nature of the substituents, the compounds of theformula (I) may contain an acidic proton, which can be removed byreaction with a base. Examples of suitable bases are hydrides,hydroxides and carbonates of lithium, sodium, potassium, magnesium andcalcium and also ammonia, and organic amines such as triethylamine andpyridine. Such salts are likewise encompassed by the present invention.

Especially preferred are herbicidal compositions according to theinvention which comprise compounds of the formula (I) where

-   V is a radical (V1), (V3) or (V4),    where the symbols and indices have the following meanings:-   R is hydrogen or (C₁-C₄)alkoxycarbonyl;-   R¹ is (C₃-C₈)cycloalkyl or (C₁-C₄)alkyl-(C₃-C₈)cycloalkyl-   R⁵ is (C₁-C₁₀)alkyl, (C₁-C₄)alkoxy or two radicals R⁵ together are    (C₂-C₆)alkylene;-   R⁶ is hydroxyl, (C₁-C₄)alkoxy or phenylthio;-   R⁷ is (C₁-C₄)alkyl or (C₃-C₇)cycloalkyl,-   R⁸ is C₁-C₄ (alkylcarbonyl), (C₁-C₄)alkoxycarbonyl or cyano;-   m is 0, 1 or 2;    and Z is a radical (Z1),    where the symbols and indices have the following meanings:-   R⁹ radicals are identical or different and are nitro, halogen,    (C₁-C₁₀)haloalkyl, (C₁-C₁₀)alkylsulfonyl, (C₁-C₁₀)haloalkoxy,    (C₁-C₁₀)alkoxy-(C₁-C₁₀)-alkyl, (C₁-C₁₀)haloalkoxy-(C₁-C₁₀)alkyl,    (C₁-C₄)alkoxy-(C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,    (C₃-C₆)-cycloalkyl-(C₁-C₄)-alkoxy, (C₃-C₆)cycloalkoxy-(C₁-C₄)-alkyl,    (C₁-C₁₀)alkoxy-(C₁-C₁₀)alkoxy,    2-tetrahydrofuranyl-(C₁-C₄)alkoxy-(C₁-C₄)-alkyl, or heterocyclyl,    which is unsubstituted or substituted by, for example, one or more    radicals selected from the group consisting of halogen,    (C₁-C₁₀)alkoxy, (C₁-C₁₀)haloalkoxy, (C₁-C₁₀)alkylthio, hydroxyl,    amino, nitro, carboxyl, cyano, azido, (C₁-C₁₀)alkoxycarbonyl,    (C₁-C₁₀)alkylcarbonyl, formyl, carbamoyl, mono- and    di-(C₁-C₁₀)alkylaminocarbonyl, acylamino, mono- and    di-(C₁-C₁₀)alkylamino, (C₁-C₁₀)alkylsulfinyl,    (C₁-C₁₀)haloalkylsulfinyl, (C₁-C₁₀)alkylsulfonyl,    (C₁-C₁₀)haloalkylsulfonyl or unsubstituted or substituted    (C₁-C₁₀)alkyl such as (C₁-C₁₀)haloalkyl, (C₁-C₁₀)alkoxyalkyl,    (C₁-C₁₀)haloalkoxyalkyl, (C₁-C₁₀)alkylthioalkyl,    (C₁-C₁₀)hydroxyalkyl, (C₁-C₁₀)aminoalkyl, (C₁-C₁₀)nitroalkyl,    (C₁-C₁₀)carboxyalkyl, (C₁-C₁₀)cyanoalkyl or (C₁-C₁₀)azidoalkyl,-   q is 0, 1, 2, 3, 4 or 5, preferably 2 or 3.

Likewise especially preferred are compositions according to theinvention which comprise the compounds of the formula (I) where thesymbols and indices have the following meanings:

-   V is the radical (V 2);-   R² is hydrogen, (C₁-C₄)-alkyl or (C₁-C₄)-alkoxy;-   R³ is hydrogen or (C₁-C₄)-alkylsulfonyl;-   R⁴ is methyl, ethyl or n-propyl;-   Z is the radical (Z 1);-   R⁹ radicals are identical or different and are nitro, halogen,    (C₁-C₄)haloalkyl or (C₁-C₄)alkylsulfonyl;-   q is 2 or 3.

Very especially preferred are compositions according to the inventionwhich comprise the compounds of the formula (I) where the symbols andindices have the following meanings:

-   V is a radical (V 1) or (V 3);-   R is hydrogen, methoxycarbonyl or ethoxycarbonyl;-   R¹ is cyclopropyl;-   R⁵ is methyl;-   R⁶ is hydroxyl;-   m is 0, 1 or 2;-   Z is the radical (Z 1);-   R⁹ radicals are identical or different and are nitro, chlorine,    fluorine, bromine, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkylsulfonyl,    (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,    (C₁-C₄)-haloalkoxy-(C₁-C₄)-alkyl, 2-tetrahydrofuranyl-methoxymethyl,    (C₁-C₂)alkoxy-(C₁-C₂)alkoxy-(C₁-C₂)alkoxy-(C₁-C₂)-alkyl,    (C₃-C₆)-cycloalkoxy-(C₁-C₂)alkyl, (C₃-C₆)-cycloalkyl-(C₁-C₂)-alkoxy,    (C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy or are 4,5-dihydroisoxazol-3-yl which    is substituted by a radical selected from the group consisting of    cyanomethyl, ethoxymethyl and methoxymethyl,-   q is 2 or 3.

Likewise especially preferred are compositions according to theinvention which comprise the compounds of the formula (I) where thesymbols and indices have the following meanings:

-   V is the radical (V 2);-   R² is hydrogen, methyl or ethyl;-   R³ is hydrogen, methylsulfonyl or ethylsulfonyl;-   R⁴ is methyl, ethyl or n-propyl;-   Z is the radical (Z 1);-   R⁹ radicals are identical or different and are methylsulfonyl,    ethylsulfonyl, chlorine, bromine, fluorine, trifluoromethyl,    (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy or    (C₁-C₄)haloalkoxy-(C₁-C₄)-alkyl;-   q is 2 or 3.

Examples of especially preferred compounds of the formula (I) are thosementioned in the following table, and the compound isoxachlortole (A17).

Mixtures of two or more compounds of the formula (I) may also be used ascomponent A).

Unless specifically defined otherwise, the following definitionsgenerally apply to the radicals in the formulae for (I) and (II) and theformulae which follow.

If the term acyl radical is used in the present description, this is tobe understood as meaning the radical of an organic acid which originatesformally by eliminating an OH group from the organic acid, for examplethe radical of a carboxylic acid and radicals of acids derivedtherefrom, such as thiocarboxylic acid, unsubstituted or N-substitutediminocarboxylic acids or the radicals of carbonic monoesters,unsubstituted or N-substituted carbamic acids, sulfonic acids, sulfinicacids, phosphonic acids or phosphinic acids.

An acyl radical is preferably formyl or acyl selected from the groupCO—R^(z), CS—R^(z), CO—OR^(z), CS—OR^(z), CS—SR^(z), SOR^(z) orSO₂R^(z), where R^(z) denotes in each case a C₁-C₁₀ hydrocarbon radicalsuch as C₁-C₁₀-alkyl or C₆-C₁₀-aryl which is unsubstituted orsubstituted, for example by one or more substituents selected from thegroup consisting of halogen, such as F, Cl, Br, I, alkoxy, haloalkoxy,hydroxy, amino, nitro, cyano or alkylthio, or R^(z) denotesaminocarbonyl or aminosulfonyl, the two last-mentioned radicals beingunsubsituted, N-monosubstituted or N,N-disubstituted, for example bysubstituents selected from the group consisting of alkyl or aryl. Acyldenotes, for example, formyl, haloalkylcarbonyl, alkylcarbonyl such as(C₁-C₄)alkylcarbonyl, phenylcarbonyl, it being possible for the phenylring to be substituted, or alkyloxycarbonyl, such as(C₁-C₄)alkyloxycarbonyl, phenyloxycarbonyl, benzyloxycarbonyl,alkylsulfonyl, such as (C₁-C₄)alkylsulfonyl, alkylsulfinyl, such asC₁-C₄(alkylsulfinyl), N-alkyl-1-iminoalkyl, such asN—(C₁-C₄)-1-imino-(C₁-C₄)alkyl and other radicals of organic acids.

Carbon-containing radicals are organic radicals containing at least onecarbon atom, preferably 1 to 40 carbon atoms, especially preferably 1 to30 carbon atoms, very especially, preferably 1 to 20 carbon atoms, andadditionally at least one atom of one or more other elements of thePeriodic Table such as H, Si, N, P, O, S, F, Cl, Br or I. Examples ofcarbon-containing radicals are unsubstituted or substituted hydrocarbonradicals which can be bonded to the skeleton directly or by a heteroatom such as Si, N, S, P or O, unsubstituted or substituted heterocyclylradicals which can be bonded to the skeleton directly or via a heteroatom such as Si, N, S, P or O, carbon-containing acyl radicals or cyano.

The term hetero atom is to be understood as meaning elements of thePeriodic Table which are other than carbon and hydrogen, for example Si,N, S, P, O, F, Cl, Br or I.

Hydrocarbon(oxy) radicals are straight-chain, branched or cyclicunsaturated or saturated aliphatic or aromatic hydrocarbon(-oxy)radicals, for example alkyl, alkenyl, alkynyl or carbocyclic rings suchas cycloalkyl, cycloalkenyl or aryl and the hydrocarbonoxy radicalscorresponding to these hydrocarbon radicals, such as alkoxy, alkenyloxy,alkynyloxy, cycloalkoxy, cycloalkenyloxy or aryloxy; aryl in thiscontext means a mono-, bi- or polycyclic aromatic system, for examplephenyl, naphthyl, tetrahydronaphthyl, indenyl, indanyl, pentalenyl,fluorenyl and the like, preferably phenyl; a hydrocarbon radicalpreferably denotes alkyl, alkenyl or alkynyl having 1 to 30 carbon atomsor cycloalkyl having 3, 4, 5, 6 or 7 ring atoms or phenyl. Substitutedradicals, such as substituted hydrocarbon(-oxy) radicals, for examplesubstituted alkyl, alkenyl, alkynyl or carbocyclic rings such ascycloalkyl, cycloalkenyl or aryl, and the hydrocarbonoxy radicalscorresponding to these hydrocarbon radicals, such as alkoxy, alkenyloxy,alkynyloxy, cycloalkoxy, cycloalkenyloxy or phenoxy, or substitutedheterocyclyl radicals, denote, for example, a substituted radicalderived from the unsubstituted skeleton, where the substituents denote,for example, one or more, preferably 1, 2 or 3, radicals selected fromthe group consisting of halogen, alkoxy, haloalkoxy, alkylthio,hydroxyl, amino, nitro, carboxy, cyano, azido, alkoxycarbonyl,alkylcarbonyl, formyl, carbamoyl, mono- and dialkylaminocarbonyl,substituted amino, such as acylamino, mono- and dialkylamino, andalkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl and,in the case of cyclic radicals, also unsubstituted or substituted alkylsuch as haloalkyl, alkoxyalkyl, haloalkoxyalkyl, alkylthioalkyl,hydroxyalkyl, aminoalkyl, nitroalkyl, carboxyalkyl, cyanoalkyl orazidoalkyl and unsaturated aliphatic radicals which correspond to theabovementioned saturated hydrocarbon-containing radicals, such asalkenyl, alkynyl, alkenyloxy, alkynyloxy and the like. In the case ofradicals with carbon atoms, those having from 1 to 4 carbon atoms, inparticular 1 or 2 carbon atoms, are preferred. Preferred are, as a rule,substituents selected from the group consisting of halogen, for examplefluorine and chlorine, (C₁-C₄)alkyl, preferably methyl or ethyl,(C₁-C₄)haloalkyl, preferably trifluoromethyl, (C₁-C₄)alkoxy, preferablymethoxy or ethoxy, (C₁-C₄)haloalkoxy, nitro and cyano. Especiallypreferred in this context are the substituents methyl, methoxy andchlorine.

The carbon-containing radicals such as alkyl, alkoxy, haloalkyl,haloalkoxy, alkylamino and alkylthio and the corresponding unsaturatedand/or substituted radicals can be in each case straight-chain orbranched in the carbon skeleton. Unless specified otherwise, the lowercarbon skeletons, for example those having 1 to 6 carbon atoms or, inthe case of unsaturated groups, those having 2 to 6 carbon atoms, arepreferred for these radicals. Alkyl radicals, also in the compositemeanings such as alkoxy, haloalkyl and the like, are, for example,methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls,such as n-hexyl, i-hexyl and 1,3-dimethylbutyl, heptyls, such asn-heptyl, 1-methylhexyl and 1,4-dimethylpentyl; alkenyl and alkynylradicals have the meanings of the unsaturated radicals which arepossible and which correspond to the alkyl radicals; for example,alkenyl is allyl, 1-methylprop-2-en-1-yl, 2-methyl-prop-2-en-1-yl,but-2-en-1-yl, but-3-en-1-yl, 1-methyl-but-3-en-1-yl and1-methyl-but-2-en-1-yl; alkynyl is, for example, propargyl,but-2-yn-1-yl, but-3-yn-1-yl, 1-methyl-but-3-yn-1-yl.

Cycloalkyl is preferably a cyclic alkyl radical having 3 to 8,preferably 3 to 7, especially preferably 3 to 6, carbon atoms, forexample cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.Cycloalkenyl and cycloalkynyl denote corresponding unsaturatedcompounds.

Halogen is fluorine, chlorine, bromine or iodine. Haloalkyl, haloalkenyland haloalkynyl are alkyl, alkenyl or alkynyl, each of which ispartially or fully substituted by halogen, preferably by fluorine,chlorine and/or bromine, in particular by fluorine or chlorine, forexample CF₃, CHF₂, CH₂F, CF₃CF₂, CH₂FCHCl, CCl₃, CHCl₂, CH₂CH₂Cl.Haloalkoxy is, for example, OCF₃, OCHF₂, OCH₂F, CF₃CF₂O, OCH₂CF₃ andOCH₂CH₂Cl. The same applies analogously to other halogen-substitutedradicals.

A hydrocarbon radical can be an aromatic hydrocarbon radical such asaryl or an aliphatic hydrocarbon radical, an aliphatic hydrocarbonradical generally being a straight-chain or branched saturated orunsaturated hydrocrabon radical, preferably having 1 to 18, especiallypreferably 1 to 12, carbon atoms, for example alkyl, alkenyl or alkynyl.

Aliphatic hydrocarbon radical preferably means alkyl, alkenyl or alkynylhaving up to 12 carbon atoms; the same applies analogously to analiphatic hydrocarbon radical in a hydrocarbonoxy radical.

A ring denotes a carbocyclic or heterocyclic mono-, bi- or polycyclicunsubstituted or substituted ring system which is saturated, unsaturatedor aromatic. Examples of carbocyclic rings are aryl, cycloalkyl orcycloalkenyl.

Aryl is, in general, a mono-, bi- or polycyclic aromatic hydrocarbonradical having preferably 6-20 carbon atoms, with preference 6 to 14carbon atoms, especially preferably 6 to 10 carbon atoms, which may havefuzed to them mono-, bi- or polycyclic, unsubstituted or substitutedaromatic heterocyclyl or mono-, bi- or polycyclic, unsubstituted orsubstituted saturated or unsaturated carbocyclyl, for example cycloalkylor cycloalkenyl, or mono-, bi- or polycyclic, unsubstituted orsubstituted saturated or unsaturated heterocyclyl. Examples of arylradicals are phenyl, naphthyl, tetrahydronaphthyl, indenyl, indanyl,pentalenyl and fluorenyl, especially preferably phenyl.

Heterocyclic ring, heterocyclic radical or heterocyclyl denotes a mono-,bi- or polycyclic unsubstituted or substituted ring system which issaturated, unsaturated and/or aromatic and contains one or more,preferably 1 to 4, hetero atoms, preferably selected from the groupconsisting of N, S and O.

Preferred are saturated heterocycles having 3 to 7 ring atoms and one ortwo hetero atoms selected from the group consisting of N, O and S, thechalcogens not being adjacent. Especially preferred are monocyclic ringshaving 3 to 7 ring atoms and one hetero atom selected from the groupconsisting of N, O and S, and also morpholine, dioxolane, piperazine,imidazoline and oxazolidine. Very especially preferred saturatedheterocycles are oxirane, pyrrolidone, morpholine and tetrahydrofuran.

Also preferred are partially unsaturated heterocycles having 5 to 7 ringatoms and one or two hetero atoms selected from the group consisting ofN, O and S. Especially preferred are partially unsaturated heterocycleshaving 5 to 6 ring atoms and one hetero atom selected from the groupconsisting of N, O and S. Very especially preferred partiallyunsaturated heterocycles are pyrazoline, imidazoline and isoxazoline.

Likewise preferred is heteroaryl, for example mono- or bicyclic aromaticheterocycles having 5 to 6 ring atoms which contain one to four heteroatoms selected from the group consisting of N, O, S, the chalcogens notbeing adjacent. Especially preferred are monocyclic aromaticheterocycles having 5 to 6 ring atoms which contain one hetero atomselected from the group consisting of N, O and S, and also pyrimidine,pyrazine, pyridazine, oxazole, thiazole, thiadiazole, oxadiazole,pyrazole, triazole and isoxazole.

Very especially preferred are pyrazole, thiazole, triazole and furan.

Mono- or disubstituted amino denotes a chemically stable radicalselected from the group of the substituted amino radicals, which areN-substituted, for example, by one or two identical or differentradicals selected from the group consisting of alkyl, alkoxy, acyl andaryl; preferably monoalkylamino, dialkylamino, acylamino, arylamino,N-alkyl-N-arylamino and N-heterocycles. Preference is given to alkylradicals having 1 to 4 carbon atoms. Aryl is preferably phenyl.Substituted aryl in this context is preferably substituted phenyl. Thedefinition given further above applies to acyl in this context,preferably (C₁-C₄)alkanoyl. This also applies analogously to substitutedhydroxylamino or hydrazino.

Optionally substituted phenyl is preferably phenyl which isunsubstituted or mono- or polysubstituted, preferably up totrisubstituted, in the case of halogen such as Cl and F also up topentasubstituted, by identical or different radicals selected from thegroup consisting of halogen, (C₁-C₄)alkyl, (C₁-C₄)alkoxy,(C₁-C₄)haloalkyl, (C₁-C₄)haloalkoxy and nitro, for example o-, m- andp-tolyl, dimethylphenyls, 2-, 3- and 4-chlorophenyl, 2-, 3- and4-trifluoro- and -trichlorophenyl, 2,4-, 3,5-, 2,5- and2,3-dichlorophenyl, o-, m- and p-methoxyphenyl.

Formulae (I) and (II) also encompass all stereo isomers whose atoms arelinked topologically in the same manner, and their mixtures. Suchcompounds contain one or more asymmetric carbon atoms or else doublebonds which are not indicated specifically in the general formulae. Thestereo isomers which are possible and which are defined by theirspecific spatial form, such as enantiomers, diastereomers, Z- andE-isomers and tautomers, can be obtained from mixtures of the stereoisomers by customary methods or else be synthesized by stereoselectivereactions in combination with the use of stereochemically pure startingmaterials.

Herbicides of the formula (I) are disclosed, for example, in EP-A 0 137963, EP-A 0 352 543, EP-A 0 418 175, EP-A 0 496 631, AU-A 672 058, EP-A0 496 631, WO-A 97/13 765, WO-A 97/01 550, WO-A 97/19 087, WO-A 96/30368, WO-A 96/31 507, WO-A 96/26 192, WO-A 96/26 206, WO-A 96/10 561,WO-A 96/05 183, WO-A 96/05 198, WO-A 96/05 197, WO-A 96/05 182, WO-A97/23 491 and WO-A 97/27 187.

The documents cited contain detailed instructions on preparation methodsand starting materials. These documents are expressly referred to; theyare incorporated into the present description by reference.

The herbicidal compositions according to the invention comprisingcompounds of the formula (I) and surfactants B) have an outstandingherbicidal action and, in a preferred embodiment, superadditive effects.Owing to the improved control of the harmful plants by the herbicidalcompositions according to the invention, it is possible to reduce theapplication rate and/or to increase the safety margin. Both make sensefrom an economical and an ecological point of view. The choice of thequantities of components A)+B) to be employed, and the ratio ofcomponents A):B), depend on a whole series of factors.

In a preferred embodiment, herbicidal compositions according to theinvention comprise a synergistically active content of a combination ofthe compounds of the formula (I) with surfactants B). In this context,it must be emphasized in particular that even in combinations withapplication rates or weight ratios of A):B), where synergism cannot bedetected easily in each individual case, for example because theindividual compounds are usually employed in the combination at verydifferent application rates or else because the control of the harmfulplants is already very good, even with the individual compounds, asynergistic effect is generally inherent to the herbicidal compositionsaccording to the invention.

Components A) and B) of the herbicidal compositions according to theinvention can be formulated separately and applied by the tank mixmethod, or else they can be present together in a readymix, which canthen be applied in the customary fashion, for example in the form of aspray mixture.

The herbicidal compositions according to the invention can be formulatedin various ways, depending on the prevailing biological and/orchemico-physical parameters. Examples of suitable formulations are:wettable powders (WP), water-soluble powders (SP), water-solubleconcentrates (SL), emulsifiable concentrates (EC), emulsions (EW) suchas oil-in-water and water-in-oil emulsions, sprayable solutions,suspension concentrates (SC), oil- or water-based dispersions,oil-miscible solutions, capsule suspensions (CS), dusts (DP), granulesfor broadcasting and soil application, granules (GR) in the form ofmicrogranules, spray granules, coated granules and adsorption granules,water-dispersible granules (WG), water-soluble granules (SG), ULVformulations, microcapsules and waxes. These individual types offormulations are known in principle and are described, for example, inWinnacker-Küchler, “Chemische Technologie” [Chemical Engineering],Volume 7, C. Hauser Verlag Munich, 4th Edition. 1986, Wade vanValkenburg, “Pesticide Formulations”, Marcel Dekker, N.Y., 1973; K.Martens, “Spray Drying” Handbook, 3rd Ed. 1979, G. Goodwin Ltd. London.

The formulation auxiliaries required, such as inert materials,surfactants, solvents and further additives, are likewise known and aredescribed, for example, in Watkins, “Handbook of Insecticide DustDiluents and Carriers”, 2nd Ed., Darland Books, Caldwell N.J., H. v.Olphen, “Introduction to Clay Colloid Chemistry”; 2nd Ed., J. Wiley &Sons, N.Y.; C. Marsden, “Solvents Guide”; 2nd Ed., Interscience, N.Y.1963; McCutcheon's “Detergents and Emulsifiers Annual”, MC PubI. Corp.,Ridgewood N.J.; Sisley and Wood, “Encyclopedia of Surface ActiveAgents”, Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt,“Grenzflächenaktive Äthylenoxidaddukte” [Surface-active ethylene oxideadducts], Wiss. Verlagsgesell., Stuttgart 1976; Winnacker-Küchler,“Chemische Technologie”, Volume 7, C. Hauser Verlag Munich, 4th Edition1986.

Based on these formulations, it is also possible to prepare combinationswith other agrochemical active ingredients which differ from componentA), such as insecticides, acaricides, herbicides, fungicides, safeners,fertilizers and/or growth regulators, for example in the form ofreadymix or a tank mix.

Wettable powders are preparations which are uniformly dispersible inwater and which, in addition to the active ingredient A) and/or thesurfactant B), also contain ionic and/or nonionic surfactants (wetters,dispersants) other than surfactant B), for example polyoxyethylatedalkylphenols, polyoxyethylated fatty alcohols, polyoxyethylated fattyamines, fatty alcohol polyglycol ether sulfates, alkanesulfonates,alkylbenzenesulfonates, sodium lignosulfonate, sodium 2,2′-dinaphthylmethane-6,6′-disulfonate, sodium dibutyinapthalene-sulfonate orelse sodium oleoylmethyltaurate, besides a diluent or inert material. Toprepare the wettable powders, the herbicidal active ingredients A)and/or surfactants B) are ground finely, for example in customaryapparatuses such as hammer mills, blower mills and air-jet mills, andmixed with the formulation auxiliaries, either simultaneously or insuccession.

Emulsifiable concentrates are prepared by dissolving the activeingredient A) and/or the surfactant B) in an organic solvent, forexample butanol, cyclohexanone, dimethylformamide, xylene or elsehigher-boiling aromatics or hydrocarbons or mixtures of the organicsolvents with addition of one or more ionic and/or nonionic surfactants(emulsifiers) other than surfactant B). The following are examples ofemulsifiers which may be used: calcium alkylarylsulfonates such ascalcium dodecylbenzenesulfonate, or nonionic emulsifiers such as fattyacid polyglycol esters, alkylaryl polyglycol ethers, fatty alcoholpolyglycol ethers, propylene oxide/ethylene oxide condensates, alkylpolyethers, sorbitan esters such as, for example, sorbitan fatty acidesters or polyoxyethylene sorbitan esters such as, for example,polyoxyethylene sorbitan fatty acid esters.

Water-soluble concentrates are obtained for example by dissolving theactive ingredient A) and/or the surfactant B) in water or in awater-miscible solvent and, if appropriate, adding further additivessuch as water-soluble surfactants to the solution.

Dusts are obtained by grinding the active ingredient A) and/or thesurfactant B) with finely divided solid materials, for example talc,natural clays such as kaolin, bentonite and pyrophyllite, ordiatomaceous earth.

Suspension concentrates may be water- or oil-based. They can be preparedfor example by wet-grinding by means of commercially available beadmills with or without addition of surfactants other than surfactant B),as they have already been mentioned, for example above in the case ofthe other formulation types.

Emulsions, for example oil-in-water emulsions (EW), can be prepared forexample by means of stirrers, colloid mills and/or static mixers usingaqueous organic solvents and, if appropriate, surfactants other thansurfactant B), as they have already been mentioned, for example above inthe case of the other formulation types.

Granules can be prepared either by spraying the active ingredient A)and/or surfactant B) onto adsorptive granulated inert material or byapplying active ingredient concentrates to the surface of carriers suchas sand, kaolinites or granulated inert material with the aid ofstickers, for example polyvinyl alcohol, sodium polyacrylate or elsemineral oils. Suitable active ingredients A) and/or surfactants B) mayalso be granulated in the fashion which is conventional for theproduction of fertilizer granules, if desired as a mixture withfertilizers.

Water-dispersible granules are generally prepared by the customarymethods such as spray drying, fluid-bed granulation, disc granulation,mixing with high-speed stirrers and extrusion without a solid inertmaterial.

To prepare disc granules, fluidized-bed granules, extruder granules andspray granules, see, for example, methods in “Spray-Drying Handbook” 3rded. 1979, G. Goodwin Ltd., London; J. E. Browning, “Agglomeration”,Chemical and Engineering 1967, pages 147 et seq.; “Perry's ChemicalEngineer's Handbook”, 5th Ed., McGraw-Hill, New York 1973, pp. 8-57.

For further details on the formulation of crop protection products, see,for example, G. C. Klingman, “Weed Control as a Science”, John Wiley andSons, Inc., New York, 1961, pages 81-96 and J. D. Freyer, S. A. Evans,“Weed Control Handbook”, 5th Ed., Blackwell Scientific Publications,Oxford, 1968, pages 101-103.

As a rule, the herbicidal compositions according to the inventioncomprise 0.01 to 99% by weight, in particular 0.1 to 95% by weight, ofone or more compounds of the formula (I).

In wettable powders, the active ingredient concentration is, forexample, approximately 10 to 90% by weight, the remainder to 100% beingcomposed of customary formulation constituents and, if appropriate,surfactants B). In the case of emulsifiable concentrates, the activeingredient concentration can amount to approximately 1 to 90, preferably5 to 80, % by weight. Formulations in the form of dusts comprise 1 to30% by weight of active ingreident, in most cases 5 to 20% by weight ofactive ingredient, and sprayable solutions comprise approximately 0.05to 80, preferably 2 to 50, % by weight of active ingredient. In the caseof water-dispersible granules, the active ingredient content dependspartly on whether the active compound is present in liquid or solid formand on the granulation auxiliaries, fillers and the like which are beingused. In the case of the water-dispersible granules, for example, theactive ingredient content is between 1 and 95% by weight, preferablybetween 10 and 80% by weight.

In addition, the active ingredient formulations mentioned comprise, ifappropriate, the auxiliaries which are conventional in each case, suchas adhesives, wetters, dispersants, emulsifiers, penetrants,preservatives, antifreeze agents, solvents, fillers, carriers,colorants, antifoams, adjuvants such as mineral oils or vegetable oilsand their derivatives, evaporation inhibitors, and pH and viscosityregulators.

The herbicidal compositions according to the invention can be preparedby customary methods, for example by mixing the components with the aidof stirrers, shakers or (static) mixers.

A preferred embodiment of the present invention consists in mixing theformulations which comprise the compounds of the formula (I) withsurfactants B) and/or their formulations in the spray tank. To this end,the compounds of the formula (I) can be formulated as water-dispersiblegranules, for example on a kaolin basis, where the content of compoundsof the formula (I) can vary within wide ranges between 0.01 and 99% byweight, preferably between 0.5 and 80% by weight. In addition to thecompounds of the formula (I), these formulations may comprise furtheragrochemical active ingredients, such as safeners, for example in anamount of 0.1-50% by weight, preferably 0.540% by weight. Thesurfactants B) can be added as such or in formulated form, preferably asa liquid product such as water-soluble concentrates or emulsifiableconcentrates.

The readymixes can be obtained by preparing for example emulsifiableconcentrates or oil dispersions from compounds of the formula (I),surfactants B) and further auxiliaries. In the readymixes, the contentof compounds of the formula (I) can vary within wide limits; in general,it is between 0.01 and 99%, preferably between 0.1 and 60% by weight.The content of surfactants B) can also vary within wide limits; it isgenerally between 1 and 80% by weight, as a rule between 5 and 50% byweight. Finally, the readymixes may also comprise further agrochemicalactive ingredients, such as safeners, for example in an amount of0.01-60% by weight, preferably 0.1-40% by weight.

If appropriate, the formulations may comprise auxiliaries such assolvents, for example aromatic solvents such as xylenes or mixtures ofaromatics from the Solvesso® series, such as Solvesso® 100, Solvesso®150 or Solvesso® 200 by Exxon; aliphatic or isoparaffinic solvents suchas products from the Exxol®-D or Isopur® series by Exxon, oils ofvegetable or animal origin and their derivatives, such as rapeseed oilsor rapeseed oil methyl esters; esters such as butyl acetate; ethers suchas diethyl ether, THF or dioxane. The solvent content is preferably1-95% by weight, especially preferably 5-80% by weight. Examples offurther suitable auxiliaries are emulsifiers (preferred content: 0.1-10%by weight), dispersants (preferred content: 0.1-10% by weight) andthickeners (preferred content: 0.1-5% by weight), and, if appropriate,stabilizers such as antifoams, water binders, acid binders andcrystallization inhibitors.

The herbicidal compositions according to the invention can be employedpre- or post-emergence, for example by spraying. By employing themixtures, the product quantity required for effecting weed control canbe reduced substantially.

As a rule, the surfactants B) to be used in accordance with theinvention are applied together with the compound(s) A) or immediately insuccession, preferably in the form of a spray mixture which comprisesthe surfactants B) and the compounds A) in effective amounts and, ifappropriate, further customary auxiliaries. The spray mixture ispreferably prepared on the basis of water and/or an oil, for example ahigh-boiling hydrocarbon such as kerosene or paraffin. The herbicidalcompositions according to the invention may be formulated as the tankmix or a “readymix”.

The weight ratio of compounds A) to surfactant B) can vary within a widerange and depends, for example, on the efficacy of the herbicide. As arule, it is in the range of from 10:1 to 1:5000, preferably from 4:1 to1:2000.

In general, the application rates of the compound(s) of the formula (I)are between 0.1 and 500 g A.S./ha (A.S.=active substance, i.e.application rate based on the active compound), preferably between 0.5and 200 g of a.i./ha. The application rates of surfactants B) aregenerally between 1 and 5000 g surfactant/ha, with between 10 and 2000 gsurfactant/ha being preferred.

The concentration of the surfactants B) to be used in accordance withthe invention is, in a spray mixture, generally from 0.05 to 4% byweight, preferably 0.1 to 1% by weight, in particular 0.1 to 0.3% byweight, of surfactant.

The herbicidal compositions according to the invention have an excellentherbicidal activity against a broad range of economically importantmonocotyledonous and dicotyledonous harmful plants. The activesubstances also act efficiently on perennial weeds which produce shootsfrom rhizomes, rootstocks or other perennial organs and which aredifficult to control. In this context, it does not matter whether thesubstances are applied before sowing, pre-emergence or post-emergence.Specifically, examples may be mentioned of some representatives of themonocotyledonous and dicotyledonous weed flora which can be controlledby the compositions according to the invention, without the enumerationbeing a restriction to certain species.

Examples of weed species on which the active substance acts efficientlyare, from amongst the monocotyledons, Avena, Lolium, Alopecurus,Phalaris, Echinochloa, Digitaria, Setaria and also Cyperus species fromthe annual sector and from amongst the perennial species Agropyron,Cynodon, Imperata and Sorghum, and also perennial Cyperus species.

In the case of the dicotyledonous weed species, the range of actionextends to species such as, for example, Galium, Viola, Veronica,Lamium, Stellaria, Amaranthus, Sinapis, lpomoea, Matricaria, Abutilonand Sida from amongst the annuals, and Convolvulus, Cirsium, Rumex andArtemisia in the case of the perennial weeds.

The compositions according to the invention likewise effect outstandingcontrol of weeds which occur under the specific conditions of ricegrowing, such as, for example, Echinochloa, Sagittaria, Alisma,Eleocharis, Scirpus and Cyperus.

If the compositions according to the invention are applied to the soilsurface before germination, then the weed seedlings are either preventedcompletely from emerging, or the weeds grow until they have reached thecotyledon stage but then their growth stops, and, eventually, afterthree to four weeks have elapsed, they die completely.

If the compositions are applied post-emergence to the green parts of theplants, growth likewise stops drastically a very short time after thetreatment and the weed plants remain at the growth stage of the point oftime of application, or they die completely after a certain time, sothat in this manner competition by the weeds, which is harmful to thecrop plants, is eliminated at a very early point in time and in asustained manner.

Even though the compositions according to the invention have anexcellent herbicidal activity against monocotyledonous anddicotyledonous weeds, crop plants of economically important crops, suchas dicotyledonous crops, like soya, cotton, oilseed rape, sugarbeet, inparticular soya, or Gramineae crops like wheat, barley, rye, rice ormaize are damaged not at all, or only to a negligible extent. For thesereasons, the present compounds are highly suitable for selectivelycontrolling undesired plant growth in plantings for agricultural orornamental use.

In addition, the herbicidal compositions according to the invention haveexcellent growth-regulatory properties in crop plants. They engage inthe plant metabolism in a regulatory fashion and can thus be employedfor the targetted control of plant constitutents and for facilitatingharvesting, such as, for example, by provoking desiccation and stuntedgrowth. Furthermore, they are also suitable for generally regulating andinhibiting undesired vegetative growth, without simultaneouslydestroying the plants. Inhibition of vegetative growth plays animportant role in many monocotyledonous and dicotyledonous crops becauselodging can be reduced hereby, or prevented completely.

Owing to their herbicidal and plant-growth-regulatory properties, theherbicidal compositions according to the invention can also be employedfor controlling harmful plants in crops of genetically modified plantswhich are known or are yet to be developed. As a rule transgenic plantsare distinguished by particular advantageous properties, for example byresistances to certain pesticides, in particular certain herbicides,resistances to plant diseases or pathogens of plant diseases, such ascertain insects or microorganisms such as fungi, bacteria or viruses.Other special properties relate to, for example, the harvested materialwith regard to quantity, quality, shelf life, composition and specificconstituents. Thus, transgenic plants are known which have an increasedstarch content or a modified starch quality, or others which have adifferent fatty acid composition of the harvested material.

The use of the compositions according to the invention in economicallyimportant transgenic crops of useful plants and ornamentals, for examplecereals such as wheat, barley, rye, oats, sorghum and millet, rice,cassava and maize, or else crops of sugar beet, cotton, soya, oilseedrape, potato, tomato, pea and other vegetables, is preferred. Thecompositions according to the invention can preferably be employed asherbicides in crops of useful plants which are resistant, or have beenmade resistant by genetic engineering, to the phytotoxic effects of theherbicides.

When using the herbicidal compositions according to the invention intransgenic crops, effects are frequently observed in addition to theeffects against harmful plants to be observed in other crops, which arespecific for application in the transgenic crop in question, for examplea modified or specifically widened wheat spectrum which can becontrolled, modified application rates which may be employed forapplication, preferably good combining ability with the herbicides towhich the transgenic crop is resistant, and an effect on growth andyield of the transgenic crop plants.

The subject matter of the invention is thus also the use of thecompositions according to the invention as herbicides for controllingharmful plants, preferably in plant crops, it also being possible forthe plant crops to be transgenic plant crops.

The herbicidal compositions according to the invention can also beemployed nonselectively for controlling undesired vegetation, forexample on verges, squares, industrial terrain and railwayinstallations.

Owing to the relatively low application rate of the herbicidalcompositions according to the invention, they are, in general, alreadyvery well tolerated. In particular, a reduction in the absoluteapplication rate is achieved with the combinations according to theinvention, compared with the individual use of a herbicidal activeingredient.

If it is desired to increase the tolerance and/or selectivity of theherbicidal compositions according to the invention even further, it maybe advantageous to apply them jointly in a mixture or staggered in timein succession together with safeners or antidotes.

Examples of compounds which are suitable as safeners or antidotes forthe herbicidal compositions according to the invention are known, forexample, from EP-A-333 131 (ZA-89/1960), EP-A-269 806 (U.S. Pat. No.4,891,057), EP-A-346 620 (AU-A-89/34951) and the international patentapplications PCT/EP 90/01966 (WO-91108202) and PCT/EP 90102020(WO-911078474) and the literature cited therein or can be prepared bythe processes described therein. Other suitable safeners are known fromEP-A-94 349 (U.S. Pat. No. 4,902,304), EP-A-191 736 (U.S. Pat. No.4,881,966) and EP-A-0 492 366 and the literature cited therein.

In a preferred embodiment, the herbicidal compositions of the presentinvention therefore comprise an additional content of C) one or morecompounds which act as safeners or antidotes.

Preferred antidotes or safeners or groups of compounds which aresuitable as safeners or antidotes in the herbicidal compositionsaccording to the invention are, inter alia:

-   a) compounds of the dichlorophenylpyrazolyl-3-carboxylic acid type,    preferably compounds such as methyl    1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylate    (mefenpyr-diethyl, compound C1-1) and related compounds as they are    described in the international application WO 91/07874 (PCT/EP    90102020);-   b) dichlorophenylpyrazolecarboxylic acid derivatives, preferably    compounds such as ethyl    1-(2,4-dichlorophenyl)-5-methyl-pyrazole-3-carboxylate (compound    C1-2), ethyl    1-(2,4-dichlorophenyl)-5-isopropyl-pyrazole-3-carboxylate (compound    C1-3), ethyl    1-(2,4-dichlorophenyl)-5-(1,1-di-methyl-ethyl)pyrazole-3-carboxylate    (compound C1-4), ethyl 1-(2,4-dichlorophenyl)-5-phenyl    pyrazole-3-carboxylate (compound C₁₋₅) and related compounds as they    are described in EP-A-0 333 131 and EP-A-0 269 806;-   c) compounds of the triazolecarboxylic acid type, preferably    compounds such as ethyl    1-(2,4-dichlorophenyl)-5-trichloromethyl-(1H)-1,2,4-triazole-3-carboxylate    (compound C₁₆, fenchlorozole-ethyl) and related compounds (see    EP-A-0 174 562 and EP-A-0 346 620);    -   d) compounds of the dichlorobenzyl-2-isoxazoline-3-carboxylic        acid type, compounds of the 5-benzyl- or        5-phenyl-2-isoxazoline-3-carboxylic acid type, preferably        compounds such as ethyl        5-(2,4-dichlorobenzyl)-2-isoxazoline-3-carboxylate (compound        C1-7) or ethyl 5-phenyl-2-isoxazoline-3-carboxylate (compound        C1-8) and related compounds as they are described in        International Patent Application WO 91/08202 (PCT/EP 90/01966);-   e) compounds of the 8-quinolinoxyacetic acid type, preferably    compounds such as    1-methyl-hex-1-yl(5-chloro-8-quinolinoxy)acetate(cloquintocet-mexyl,    C2-1), 1,3-dimethylbut-1-yl(5-chloro-8-quinolinoxy)acetate(C2-2),    4-allyl-oxybutyl(5-chloro-8-quinolinoxy)acetate(C2-3),    1-allyl-oxy-prop-2-yl (5-chloro-8-quinolinoxy)acetate(C2-4),    ethyl(5-chloro-8-quinolinoxy)acetate (C2-5),    methyl(5-chloro-8-quinolinoxy)acetate(C2-6), allyl    (5-chloro-8-quinolinoxy)acetate(C2-7),    2-(2-propylidene-iminoxy)-1-ethyl    (5-chloro-8-quinolinoxy)acetate(C2-8), 2-oxoprop-1-yl    (5-chloro-8-quinolinoxy)acetate(C2-9) and related compounds as they    are described in EP-A-0 086 750, EP-A-0 094 349 and EP-A-0 191 736    or EP-A-0 492 366;-   f) compounds of the (5-chloro-8-quinolinoxy) malonic acid type,    preferably compounds such as diethyl(5-chloro-8-quinolinoxy)    malonate, diallyl (5-chloro-8-quinolinoxy) malonate, methyl    ethyl(5-chloro-8-quinolinoxy) malonate and related compounds as they    have been described and proposed in German Patent Application EP-A-0    582 198;-   g) active ingredients of the type of the phenoxyacetic- or    -propionic acid derivatives or of the aromatic carboxylic acids such    as, for example, 2,4-dichlorophenoxyacetic acid ester (2,4-D),    4-chloro-2-methylphenoxypropionic acid ester (mecoprop), MCPA or    3,6-dichloro-2-methoxybenzoic acid (and its ester) (dicamba);-   h) compounds of the 5,5-diphenyl-2-isoxazoline-3-carboxylic acid    type, preferably ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylate    (isoxadifen-ethyl, C3-1);-   i) compounds which are known as safeners for, for example, rice such    as fenclorim (=4,6-dichloro-2-phenylpyrimidine, Pesticide Manual,    11th Edition, 1997, pp. 511-512), dimepiperate    (═S-1-methyl-1-phenylethyl piperidine-1-thiocarboxylate, Pesticide    Manual, 11th Edition, 1997, pp. 404405), daimuron    (=1-(1-methyl-1-phenylethyl)-3-p-tolylurea, Pesticide Manual, 11th    Edition, 1997, p. 330), cumyluron    (=3-(2-chlorophenylmethyl)-1-(1-methyl-1-phenyl-ethyl)-urea,    JP-A-60/087,254), methoxyphenone    (=3,3′-dimethyl-4-methoxy-benzophenone, CSB    (=1-bromo-4-(chloromethylsulfonyl)benzene, CAS Reg. No. 54091-064).

Moreover, at least some of the abovementioned compounds are described inEP-A-0 640 587, which is herewith referred to for disclosure purposes.

-   j) A further important group of compounds which are suitable as    safeners and antidotes is disclosed in WO 95107897.

The safeners (antidotes) of the above groups a) to j) reduce or suppressphytotoxic effects which may occur when using the herbicidalcompositions according to the invention in crops of useful plants,without adversely affecting the efficacy of the herbicides againstharmful plants. Thus, the field of application of the herbicidalcompositions according to the invention can be widened substantially,and, in particular, the use of safeners makes possible the use ofcombinations which could previously only be employed with limited orinsufficient success, i.e. combinations which, when applied withoutsafener and in low dosages with a narrow spectrum of action, lead toinsufficient control of the harmful plants.

The herbicidal compositions according to the invention and theabovementioend safeners can be applied together (as a readymix or by thetank mix method) or in succession in any desired sequence. The weightratio of safener:herbicide (compound(s) of the formula (I)) can varywithin wide limits and is preferably in the range of from 1:100 to100:1, in particular of from 1:10 to 10:1. The amounts of herbicide(s)and safener(s) which are optimal in each case usually depend on the typeof the herbicidal composition and/or on the safener used and on thespecies of the plant stand to be treated.

Depending on their properties, the safeners of type C) can be used forpretreating the seed of the crop plant (seed treatment) or introducedinto the seed furrows prior to sowing or applied together with theherbicide mixture before or after emergence of the plants.

Pre-emergence treatment includes not only the treatment of the areaunder cultivation prior to sowing, but also the treatment of areas undercultivation where the crop has been sown, but has not emerged yet.Preferred is the concommitant use with the herbicide mixture. To thisend, tank mixes or readymixes may be employed.

Depending on the indication of the herbicide used, the application ratesof the safeners required can vary within wide limits and are, as a rule,in the range of from 0.001 to 1 kg, preferably from 0.005 to 0.2 kg, ofactive ingredient per hectare. Subject matter of the present inventionis also a method of controlling undesired plants, preferably in plantcrops, which comprises applying a herbicidally effective amount of theherbicidal composition according to the invention to the plants, plantparts, seeds of the plants, or the area under cultivation.

A preferred variant of the method is to apply the herbicidalcompositions according to the invention in the form of tank mixes, wherethe individual components (for example in the form of formulations) aremixed together in the tank with water or an oil, and the resulting spraymixture is applied. Since the crop plant tolerance of the combinationsaccording to the invention is excellent while simultaneously effectingvery good control of the harmful plants, the combinations can beregarded as selective. In a preferred modification of this method,herbicidal compositions are therefore employed for the selective controlof undesired plants.

The herbicidal compositions can be applied in the customary fashion, forexample with water and/or oil as carrier, at spray mixture rates ofapproximately 0.5-4000, preferably 100 to 1000, liters/ha. Anapplication of the compositions by the low-volume and ultra-low volumemethods (ULV) is also possible, as is their application in the form ofgranules and microgranules.

A preferred use relates to the application of herbicidal compositions,which exhibit contents of components A) and B) in a synergisticallyactive amount. The invention also includes mixtures of one or morecomponents A), preferably A1, A2, A3 and/or A4, and one or morecomponent B), if appropriate in combination with one or more safenersC).

As preferred examples for the herbicidal compositions according to theinvention, the following combinations of A1, A2, A3 and/or A4 withsurfactants B) may be mentioned, without this constituting a limitationto combinations which have been mentioned explicitly:

-   A1 in combination with one of the surfactants of group B1 to B105    (see Table 1)-   A2 in combination with one of the surfactants of the group B1 to    B105 (see Table 1)-   A3 in combination with one of the surfactants of the group B1 to    B105 (see Table 1)-   A4 in combination with one of the surfactants of the group B1 to    B105 (see Table 1)-   A5 in combination with one of the surfactants of the group B1 to    B105 (see Table 1)-   A6 in combination with one of the surfactants of the group B1 to    B105 (see Table 1)-   A7 in combination with one of the surfactants of the group B1 to    B105 (see Table 1)-   A8 in combination with one of the surfactants of the group B1 to    B105 (see Table 1)-   A9 in combination with one of the surfactants of the group B1 to    B105 (see Table 1)-   A10 in combination with one of the surfactants of the group B1 to    B105 (see Table 1)-   A11 in combination with one of the surfactants of the group B1 to    B105 (see Table 1)-   A12 in combination with one of the surfactants of the group B1 to    B105 (see Table 1)-   A13 in combination with one of the surfactants of the group B1 to    B105 (see Table 1)-   A14 in combination with one of the surfactants of the group B1 to    B105 (see Table 1)-   A15 in combination with one of the surfactants of the group B1 to    B105 (see Table 1)-   A16 in combination with one of the surfactants of the group B1 to    B105 (see Table 1)-   A17 in combination with one of the surfactants of the group B1 to    B105 (see Table 1)

The use of a safener may be advantageous in the abovementionedcombinations since this makes it possible to reduce potential damage tothe crop plant which may be caused by herbicides A) or otherherbicidally active ingredients.

In addition, and to complement the characteristics, the herbicidalcompositions of the present invention may additionally comprise one, twoor more agrochemical active ingredients (for example, herbicides,insecticides or fungicides) other than component A), in general in minorquantities.

This leads to a large number of possibilities of combining severalactive ingredients with each other and of employing them jointly forcontrolling harmful plants, preferably in plant crops, without deviatingfrom the inventive concept.

In conclusion, it can be said that the joint application of compounds ofthe formula (I) with one or more surfactants B) results in anoutstanding herbicidal action. In a preferred embodiment, the action ofthe herbicidal compositions according to the invention exceeds theaction of the individual components employed when used singly.

These effects permit, inter alia, a reduced application rate, thecontrol of a broader spectrum of dicotyledonous and monocotyledonousweeds, the closure of control gaps, also with regard to resistantspecies, more rapid and safer action, complete control of the harmfulplants with only one or few applications, and a widened period of use.

The abovementioned characteristics are required in weed control practicein order to keep agricultural crops free from undesired competing plantsand thus guaranteeing and/or increasing the yields in terms of qualityand quantity. The state of the art is exceeded markedly by thecombinations according to the invention with regard to theabove-described properties. Moreover, the combinations according to theinvention allow in the most outstanding fashion the control of otherwiseresistant harmful plants.

EXAMPLES

Seeds or rhizome pieces of monocotyledonous and dicotyledonous weedplants were placed in sandy loamy soil in plastic pots, covered withsoil and grown in the greenhouse under favorable growth conditions.Three weeks after sowing, the test plants were treated in the three-leafstage. The compounds according to the invention which were formulated inthe form of wettable powders or emulsion concentrates were sprayed ontothe green plant parts at an application rate of 600 to 800 l of water/ha(converted), in various dosages. After the test plants had been left tostand in the greenhouse under optimum growth conditions for 3 to 4 weeksthe effect of the preparations was scored visually by comparison withuntreated controls. The compositions according to the invention exhibita good herbicidal activity against economically important harmfulplants.

For example, the action of herbicide A1 (application rate 200 g/ha) andof herbicides A4, A6 and A9 (application rates in each case 80 g/ha) isincreased markedly by combining them with a surfactant such as Genapol X150, Genapol X 200, Sapogenat T 130, Sapogenat T 200, Sapogenat T 300,Sapogenat T 400, Sapogenat T 500 or Genapol O 200 at application ratesof, for example, 50 g/ha, 10 g/ha, 300 g/ha and 500 g/ha in comparisonwith, for example, the application of the abovementioned herbicideswithout surfactant or with a surfactant with a low ethylene oxide unitcontent such as Genapol O 060 or Sapogenat T 040 (6 and 4 ethylene oxideunits, respectively).

The comparative examples mentioned in the table hereinbelow demonstratethe particularly high herbicidal action of the compositions according tothe invention (Nos 4, 5 and 6) in comparison with the action of theherbicide without surfactant (No. 1) or in comparison with the action ofthe herbicide together with surfactants with a low ethylene oxide unitcontent (Nos 2 and 3).

The herbicides were formulated in each case as wettable powders with anactive ingredient content of 20%. Herbicide Surfactant Herbicidal actionagainst No. (80 g/ha) (300 g/ha) Monocots Dicots 1 A4 —  3% 29% 2 A4Genapol O 080 12% 55% 3 A4 Sapogenat T 040 12% 44% 4 A4 Genapol O 20038% 61% 5 A4 Sapogenat T 300 40% 57% 6 A4 Sapogenat T 500 49% 72%

1. A herbicidal composition comprising A) one or more compounds of theformula (I)

where V is an unsubstituted or substituted heterocyclyl radical or aradical —CR^(α)═CR^(β)R^(β1), where R^(α) and R^(β) are identical ordifferent carbon-containing C₁-C₄₀ radicals which together can form anunsubstituted or substituted ring, and R^(β1) is OH or acarbon-containing C₁-C₄₀ radical, and Z is an unsubstituted orsubstituted aryl radical, and B) one or more surfactants comprising, asstructural element, at least 10, alkylene oxide units.
 2. A herbicidalcomposition as claimed in claim 1 comprising, as component B), one ormore surfactants of the general formula (II)R^(γ)-(EO)_(x)(PO)_(y)(EO)_(z)-R^(δ)  (II) where EO denotes an ethyleneoxide unit, PO denotes a propylene oxide unit, x denotes an integer from1 to 50, y denotes an integer from 0 to 50, z denotes an integer from 0to 50, where the total (x+y+z)≧10 and ≦150, and R^(γ) denotes OH, anunsubstituted or substituted C₁-C₄₀-hydrocarbonoxy radical, an O-acylradical or NR^(I)R^(II) or [NR^(I)R^(II)R^(III)]^(⊕)X^(⊖), where R^(I),R^(II) and R^(III) are identical or different and denote H or anunsubstituted or substituted C₁-C₃₀-hydrocarbon radical which canoptionally be bound via a group (EO)_(w), where w is an integer from 1to 50, X^(⊖) is an anion, and R^(δ) denotes H, an unsubstituted orsubstituted C₁-C₄₀-hydrocarbon radical, an acyl radical or NR^(I)R^(II)or [NR^(I)R^(II)R^(III)]^(⊕)X^(⊖), where R^(I), R^(II) and R^(III) areidentical or different and denote H or an unsubstituted or substitutedC₁-C₃₀-hydrocarbon radical which can optionally be bound via a group(EO)_(w), where w is an integer from 1 to 50, X^(⊖) is an anion.
 3. Aherbicidal composition as claimed in claim 1, comprising, as componentA), a compound of the formula (I)

in which V is a radical selected from the group (VI) to (V4),

where the symbols and the indices have the following meanings: R ishydrogen, (C₁-C₁₀)alkoxycarbonyl, (C₁-C₁₀)haloalkoxycarbonyl,(C₁-C₁₀)alkylsulfonyl, (C₁-C₁₀)alkylsulfinyl, (C₁-C₁₀)alkylthio, COOH orcyano; R¹ is hydrogen or a (C₁-C₁₀)carbon-containing radical such as(C₁-C₁₀)alkyl, (C₂-C₁₀)alkenyl, (C₂-C₁₀)alkynyl, (C₃-C₁₀)cycloalkyl,(C₃-C₁₀)cycloalkenyl, (C₁-C₁₀)alkyl-(C₃-C₁₀)cycloalkyl,(C₃-C₁₀)halocycloalkyl, (C₁-C₁₀)alkylthio-cycloalkyl, (C₁-C₁₀)haloalkylor (C₂-C₁₀)haloalkenyl; R² is hydrogen, (C₁-C₁₀)alkyl, (C₁-C₁₀)alkoxy,(C₁-C₁₀)haloalkyl, halogen, (C₁-C₁₀)haloalkoxy, cyano or nitro; R³ ishydrogen or a (C₁-C₁₀)carbon-containing radical such as (C₁-C₁₀)alkyl,(C₂-C₁₀)alkenyl, (C₂-C₁₀)alkynyl, (C₁-C₁₀)haloalkyl,(C₁-C₁₀)alkoxy-(C₁-C₁₀)alkyl, (C₁-C₁₀)alkylcarbonyl,(C₁-C₁₀)alkylsulfonyl, (C₁-C₁₀)haloalkylsulfonyl, unsubstituted orsubstituted arylsulfonyl, unsubstituted or substitutedarylcarbonyl-(C₁-C₁₀)alkyl or unsubstituted or substituted aryl(C₁-C₁₀)alkyl; R⁴ is hydrogen or a (C₁-C₁₀)carbon-containing radicalsuch as (C₁-C₁₀)alkyl, (C₂-C₁₀)alkenyl, (C₂-C₁₀)alkynyl,(C₁-C₁₀)haloalkyl, phenyl or benzyl; R⁵ is a (C₁-C₁₂)carbon-containingradical such as (C₁-C₁₀)alkyl, (C₁-C₁₀)alkoxy,(C₁-C₁₀)alkoxy-(C₁-C₁₀)alkyl, (C₁-C₁₀)dialkoxy-(C₁-C₁₀)alkyl,(C₁-C₁₀)alkylthio, halogen, substituted or unsubstituted aryl,tetrahydropyran-4-yl, tetrahydro-pyran-3-yl, tetrahydrothiopyran-3-yl,1-methylthio-cyclopropyl, 2-ethylthio propyl, or two radicals R⁵together are (C₂-C₁₀)alkylene; R⁶ is hydroxyl or a(C₁-C₁₀)carbon-containing radical such as (C₁-C₁₀)alkoxy,(C₁-C₁₀)haloalkoxy, formyloxy, (C₁-C₁₀)alkylcarbonyloxy,(C₁-C₁₀)alkylsulfonyloxy, (C₁-C₁₀)alkylthio, (C₁-C₁₀)haloalkylthio,unsubstituted or substituted arylthio, unsubstituted or substitutedaryloxy, (C₁-C₁₀)alkylsulfinyl or (C₁-C₁₀)alkylsulfonyl; R⁷ is a(C₁-C₇)carbon-containing radical such as (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,(C₃-C₇)cycloalkyl, (C₁-C₄)alkyl-(C₃-C₇)cycloalkyl,(C₃-C₇)halocycloalkyl; R⁸ is a (C₁-C₄)carbon-containing radical such ascyano, (C₁-C₄)alkoxycarbonyl, (C₁-C₄)alkylcarbonyl,(C₁-C₄)alkylsulfonyl, (C₁-C₄)alkylsulfinyl, (C₁-C₄) alkylthio,(C₁-C₄)alkylaminocarbonyl, (C₁-C₄)dialkylaminocarbonyl; m is an integerfrom 0 to 6, where, if m≧2, the radicals R⁵ can be identical ordifferent from one another; and Z is an unsubstituted or substitutedaryl radical, preferably selected from the group (Z1) to (Z5),

where the symbols and indices have the following meanings; R⁹ radicalsare identical or different and are nitro, amino, halogen, OH, SF₅ or a(C₁-C₁₀)carbon-containing radical such as (C₁-C₁₀)alkyl,(C₂-C₁₀)alkenyl, (C₂-C₁₀)alkynyl, (C₁-C₁₀)haloalkyl,(C₂-C₁₀)haloalkenyl, (C₂-C₁₀)haloalkynyl, (C₂-C₁₀)haloalkoxy,(C₁-C₁₀)haloalkylthio, (C₁-C₁₀)alkoxycarbonyl, (C₁-C₁₀)alkylsulfonyl,(C₁-C₁₀)alkylsulfinyl, (C₁-C₁₀)alkylthio, arylsulfonyl, arylsulfinyl,arylthio, (C₁-C₁₀)alkoxy, (C₁-C₁₀)alkoxy-(C₁-C₁₀)alkoxy,(C₁-C₁₀)alkylthio-(C₁-C₁₀)-alkoxy, (C₁-C₁₀)alkylcarbonyl, (C₁-C₁₀)alkylaminosulfonyl, (C₁-C₁₀)dialkylaminosulfonyl,(C₁-C₁₀)alkylcarbamoyl,(C₁-C₁₀)dialkylcarbamoyl,(C₁-C₁₀)alkoxy-(C₁-C₁₀)alkyl, (C₁-C₁₀)haloalkoxy(C₁-C₁₀)alkyl,(C₁-C₄)alkoxy-(C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,(C₃-C₆)-cycloalkyl-(C₁-C₄)-alkoxy, (C₃-C₆)cycloalkoxy-(C₁-C₄)-alkyl,phenoxy, cyano, alkylamino, dialkylamino, unsubstituted or substitutedbenzyl, unsubstituted or substituted heteroaryl, unsubstituted orsubstituted heterocyclyl,2-tetrahydrofuranyl-(C₁-C₄)alkoxy-(C₁-C₄)-alkyl, unsubstituted orsubstituted heteroaryl-(C₁-C₁₀)alkyl or di-(C₁-C₁₀)alkylphosphono(C₁-C₁₀)alkyl; q is 0, 1, 2, 3, 4 or 5; R¹⁰ radicals are identical ordifferent and are hydrogen, (C₁-C₁₀)alkyl, halogen; R¹¹ radicals areidentical or different and are (C₁-C₁₀)alkyl, (C₂-C₁₀)alkenyl, (C₂-C₁₀)alkynyl, halogen, (C₁-C₁₀)haloalkyl, (C₂-C₁₀)haloalkenyl,(C₂-C₁₀)haloalkynyl, (C₁-C₁₀)haloalkoxy, (C₁-C₁₀)haloalkylthio,(C₁-C₁₀)alkoxycarbonyl, (C₁-C₁₀) alkylsulfonyl,(C₁-C₁₀)haloalkylsulfonyl, (C₁-C₁₀)alkylsulfinyl, (C₁-C₁₀)haloalkylsulfinyl, (C₁-C₁₀)alkylthio, (C₁-C₁₀)alkoxy,(C₁-C₁₀)alkylcarbonyl, (C₁-C₁₀)alkylaminosulfonyl,(C₁-C₁₀)dialkylaminosulfonyl, (C₁-C₁₀)alkylcarbamoyl,(C₁-C₁₀)dialkylcarbamoyl, (C₁-C₁₀)alkoxyalkyl, phenoxy, nitro, cyano,aryl or di-(C₁-C₁₀)alkylphosphono-(C₁-C₁₀)alkyl; X¹ is O, CR¹⁵R¹⁶, CHOH,C═O, C═NO(C₁-C₁₀)alkyl; X² is O, S, SO, SO₂, CH₂, NH, N(C₁-C₁₀)alkyl,NSO₂(C₁-C₁₀)alkyl; R¹⁵,R¹⁶ radicals are identical or different and arehydrogen, (C₁-C₁₀)alkyl, (C₁-C₁₀) alkoxy, (C₁-C₁₀)haloalkoxy,(C₁-C₁₀)alkylthio, (C₁-C₁₀)haloalkylthio or R¹⁵ and R¹⁶ together formone of the groups —O—(CH₂)₂—O—, —O—(CH₂)₃—O—, S—(CH₂)₂—S—, —S—(CH₂)₃—S—,—(CH₂)₄—, —(CH₂)₅—; r is 0, 1, 2 or 3; t is 1 or 2; Y¹, Y² are SO₂ orCO, with the proviso that Y¹≠Y², v is 1 or 2; U¹ together with thecarbon atoms to which it is linked forms a carbocyclic or heterocyclicring which can be aromatic or fully or partially saturated; U² is O, S,SO, SO₂, CH₂, NH, N(C₁-C₁₀)alkyl, NSO₂(C₁-C₁₀)alkyl; R¹² is hydrogen,(C₁-C₁₀)alkyl, (C₃-C₁₀)-cycloalkyl, (C₂-C₁₀)alkenyl, (C₂-C₁₀)alkynyl,optionally substituted phenyl, optionally substituted benzyl,(C₁-C₁₀)-acyl; R¹³ is an unsubstituted or substituted(C₁-C₁₀)hydrocarbon radical such as (C₁-C₁₀) alkyl or aryl; u is 0, 1 or2; R¹⁴ radicals are identical or different and are nitro, amino,halogen, SF₅ or a (C₁-C₁₀) carbon-containing radical such as(C₁-C₁₀)alkyl, (C₂-C₁₀)alkenyl, (C₂-C₁₀) alkynyl, (C₁-C₁₀)haloalkyl,(C₂-C₁₀)haloalkenyl, (C₂-C₁₀)haloalkynyl, (C₁-C₁₀) haloalkoxy,(C₁-C₁₀)haloalkylthio, (C₁-C₁₀)alkoxycarbonyl, (C₁-C₁₀)alkylsulfonyl,(C₁-C₁₀)alkylsulfinyl, (C₁-C₁₀)alkylthio, arylsulfonyl, arylsulfinyl,arylthio, (C₁-C₁₀)alkoxy, (C₁-C₁₀)alkoxy-(C₁-C₁₀)alkoxy,(C₁-C₁₀)-alkylthio-(C₁-C₁₀) -alkoxy, (C₁-C₁₀)alkylcarbonyl,(C₁-C₁₀)alkylaminosulfonyl, (C₁-C₁₀)dialkylarinosulfonyl,(C₁-C₁₀)alkylcarbamoyl, (C₁-C₁₀)dialkylcarbamoyl,(C₁-C₁₀)alkoxy-(C₁-C₁₀)alkyl, (C₁-C₁₀)haloalkoxy (C₁-C₁₀)alkyl, phenoxy,cyano, alkylamino, dialkylamino, unsubstituted or substituted benzyl,unsubstituted or substituted heteroaryl, unsubstituted or substitutedheterocyclyl, unsubstituted or substituted heteroaryl-(C₁-C₁₀)alkyl ordi-(C₁-C₁₀)alkylphosphono-(C₁-C₁₀)alkyl, and w is 0, 1, 2, 3 or
 4. 4. Aherbicidal composition as claimed in claim 1, comprising, as componentA), a compound of the formula (I) where V is a radical (V1), (V3) or(V4),

where the symbols and indices have the following meanings: R is hydrogenor (C₁-C₄)alkoxycarbonyl; R¹ is (C₃-C₈)cycloalkyl or(C₁-C₄)alkyl-(C₃-C₈)cycloalkyl R⁵ is (C₁-C₁₀)alkyl, (C₁-C₄)alkoxy or tworadicals R⁵ together are (C₂-C₆)alkylene; R⁶ is hydroxyl, (C₁-C₄)alkoxyor phenylthio; R⁷ is (C₁-C₄)alkyl or (C₃-C₇)cycloalkyl, R⁸ is C₁-C₄(alkylcarbonyl), C₁-C₄ alkoxycarbonyl or cyano; m is 0, 1 or 2; and Z isa radical (Z1),

where the symbols and indices have the following meanings: R⁹ radicalsare identical or different and are nitro, halogen, (C₁-C₁₀)haloalkyl,(C₁-C₁₀)alkylsulfonyl, (C₁-C₁₀)haloalkoxy,(C₁-C₁₀)alkoxy-(C₁-C₁₀)-alkyl, (C₁-C₁₀)haloalkoxy-(C₁-C₁₀)alkyl,(C₁-C₄)alkoxy-(C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,(C₃-C₆)-cycloalkyl-(C₁-C₄)-alkoxy, (C₃-C₆)cycloalkoxy (C₁-C₄)-alkyl,(C₁-C₁₀)alkoxy-(C₁-C₁₀)alkoxy, 2-tetrahydrofuranyl-(C₁-C₄)alkoxy-(C₁-C₄)-alkyl, or heterocyclyl, which is unsubstituted orsubstituted by, for example, one or more radicals selected from thegroup halogen, (C₁-C₁₀)alkoxy, (C₁-C₁₀)haloalkoxy, (C₁-C₁₀)alkylthio,hydroxyl, amino, nitro, carboxyl, cyano, azido, (C₁-C₁₀)alkoxycarbonyl,(C₁-C₁₀)alkylcarbonyl, formyl, carbamoyl, mono- anddi-(C₁-C₁₀)alkylaminocarbonyl, acylamino, mono- anddi-(C₁-C₁₀)alkylamino, (C₁-C₁₀)alkylsulfinyl, (C₁-C₁₀)haloalkylsulfinyl,(C₁-C₁₀)alkylsulfonyl, (C₁-C₁₀)haloalkylsulfonyl or unsubstituted orsubstituted (C₁-C₁₀)alkyl such as (C₁-C₁₀)haloalkyl,(C₁-C₁₀)alkoxyalkyl, (C₁-C₁₀)haloalkoxyalkyl, (C₁-C₁₀)alkylthioalkyl,(C₁-C₁₀)hydroxyalkyl, (C₁-C₁₀)aminoalkyl, (C₁-C₁₀)nitroalkyl,(C₁-C₁₀)carboxyalkyl, (C₁-C₁₀)cyanoalkyl or (C₁-C₁₀)azidoalkyl, q is 0,1, 2, 3, 4 or 5, preferably 2 or
 3. 5. A herbicidal composition asclaimed in claim 1 comprising, as component A), a compound of theformula (1) where the symbols and indices have the following meanings: Vis the radical (V 2); R² is hydrogen, (C₁-C₄)-alkyl or (C₁-C₄)-alkoxy;R³ is hydrogen or (C₁-C₄)-alkylsulfonyl; R⁴ is methyl, ethyl orn-propyl; Z is the radical (Z 1); R9 radicals are identical or differentand are nitro, halogen, (C₁-C₄)haloalkyl or (C₁-C₄)alkylsulfonyl; q is 2or
 3. 6. A herbicidal composition as claimed in claim 1 comprising, ascomponent A), a compound of the formula (1) where the symbols andindices have the following meanings: V is a radical (V1) or (V3); R ishydrogen, methoxycarbonyl or ethoxycarbonyl; R¹ is cyclopropyl; R⁵ ismethyl; R⁶ is hydroxyl; m is 0, 1 or 2; Z is the radical (Z 1); R⁹radicals are identical or different and are nitro, chlorine, fluorine,bromine, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkylsulfonyl, (C₁-C₄)-haloalkoxy,(C₁-C₄)-alkoxy-(C₁-C₄) -alkyl, (C₁-C₄)-haloalkoxy-(C₁-C₄)-alkyl,2-tetrahydrofuranyl methoxymethyl,(C₁-C₂)alkoxy-(C₁-C₄)alkoxy-(C₁-C₄)alkoxy-(C₁-C₄)-alkyl,(C₃-C₆)-cycloalkoxy-(C₁-C₂)alkyl, (C₃-C₆)-cycloalkyl-(C₁-C₂)-alkoxy,(C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy or are 4,5-dihydroisoxazol-3-yl which issubstituted by a radical selected from the group consisting ofcyanomethyl, ethoxymethyl and methoxymethyl, q is 2 or
 3. 7. Aherbicidal composition as claimed in claim 1 comprising, as componentA), a compound of the formula (I) where the symbols and indices have thefollowing meanings: V is the radical (V 2); R² is hydrogen, methyl orethyl; R³ is hydrogen, methylsulfonyl or ethylsulfonyl; R⁴ is methyl,ethyl or n-propyl; Z is the radical (Z 1); R⁹ radicals are identical ordifferent and are methylsulfonyl, ethylsulfonyl, chlorine, bromine,fluorine, trifluoromethyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy or(C₁-C₄)haloalkoxy-(C₁-C₄)-alkyl; q is 2 or
 3. 8. A herbicidalcomposition as claimed in claim 17, additionally comprising one or morefurther components selected from the group containing agrochemicalactive ingredients, additives conventionally used in crop protection,and formulations relating thereto.
 9. A method of controlling harmfulplants, wherein the herbicidal composition defined as in claim 1 isapplied to the plants, plant parts, seeds of the plants of the areaunder cultivation pre-emergency, post-emergency or pre- andpost-emergence.
 10. The method as claimed in claim 9 for the selectivecontrol of harmful plants in plant crops.
 11. (canceled)
 12. A processfor the preparation of the herbicidal composition defined as in one ormore of claims 1 to 8, wherein the compound(s) of the formula (I) is/aremixed with one or more surfactants B).
 13. The process as claimed inclaim 12, wherein components A) and B) are mixed with water and/or anoil by the tank mix method.
 14. The herbicidal composition of claim 3wherein compound A is a compound of the formulaV-C(O)-Z wherein V is selected from the group consisting of (V3) and(V4), and wherein Z is selected from the group consisting of Z1, Z2, Z4,and Z5.
 15. A herbicidal composition comprising A) one or more compoundsof the formula (I)

wherein V is a radical selected from the group (V2) and (V3)

R is hydrogen, methoxycarbonyl or ethoxycarbonyl; R² is hydrogen, methylor ethyl; R³ is hydrogen, methylsulfonyl or ethylsulfonyl; R⁴ is methyl,ethyl or n-propyl; R⁵ is methyl; R⁶ is hydroxyl; m is 0, 1 or 2; z isthe radical (Z1)

R⁹ is the case that V is V3, radicals are identical or different and arenitro, chlorine, fluorine, bromine, (C₁-C₄)-haloalkyl,(C₁-C₄)-alkylsulfonyl, (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,(C₁-C₄)-haloalkoxy-(C₁-C₄)-alkyl, 2-tetrahydrofuranyl-methoxymethyl,(C₁-C₂)alkoxy-(C₁-C₄)alkoxy-(C₁-C₄)-alkoxy -(C₁-C₄)-alkyl,(C₃-C₆)-cycloalkyl-(C₁-C₂)-alkoxy, (C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy or are4,5-dihydroisoxazol-3-yl which is substituted by a radical selected fromthe group consisting of cyanomethyl, ethoxymethyl and methoxymethyl; R⁹in the case that V is V2, radicals are identical or different and aremethylsulfonyl, ethylsulfonyl, chlorine, bromine, fluorine,trifluoromethyl, (C₁-C₄)-alkoxy, (C₁-C₄)haloalkoxy or(C₁-C₄)haloalkoxy-(C₁-C₄)-alkyl; q is 2 or 3; and B) one or moresurfactants of the general formula (II)R^(y)-(EO)_(x) (PO)_(y)(EO)_(z), R^(δ) where EO denotes an ethyleneoxide unit, PO denotes a propylene oxide unit, x denotes an integer from10 to 50, y denotes an integer from 0 to 50, z denotes an integer from 0to 50, where the total (x+y+z)≧10 and ≦150, and R^(γ) denotes OH, anunsubstituted or substituted (C₁-C₄₀)-hydrocarboxy radical, an O-acylradical or NR^(I)R^(II) or [NR^(I)R^(II)R^(III)]^(⊕)X^(⊖), where R^(I),R^(II) and R^(III) are identical or different and denote H or anunsubstituted or substituted C₁-C₃₀-hydrocarbon radical which canoptionally be bound via a group (EO)_(w), where w is an integer from 1to 50, X^(⊖) is an anion, and R^(δ) denotes H, an unsubstituted orsubstituted (C₁-C₄₀)-hydrocarbon radical, an acyl radical orNR^(I)R^(II) or [NR^(I)R^(II)R^(III)]^(⊕)X^(⊖), where R^(I), R^(II) andR^(III) are identical or different and denote H or an unsubstituted orsubstituted C₁-C₃₀-hydrocarbon radical which can optionally be bound viaa group (EO)_(w), where w is an integer from 1 to 50, X^(⊖) is an anion.16. A herbicidal composition as claimed in claim 15 comprising,as-component B), one or more surfactants of the general formula (II)R^(γ)-(EO)_(x)(PO)_(y)(EO)_(z)-R^(δ)  (II) where EO denotes an ethyleneoxide unit, PO denotes a propylene oxide unit, x denotes an integer from1 to 50, y denotes an integer from 0 to 50 z denotes an integer from 0to 50, where the total (x+y+z)≧10 and ≦150, and R^(γ) denotes OH, anunsubstituted or substituted C₁-C₄₀-hydrocarbonoxy radical, an O-acylradical or NR^(I)R^(II) or [NR^(I)R^(II)R^(III)]^(⊕)X^(⊖), where R^(I),R^(II) and R^(III) are identical or different and denote H or anunsubstituted or substituted C₁-C₃₀-hydrocarbon radical which canoptionally be bound via a group (EO)_(w), where w is an integer from 1to 50, X^(⊖) is an anion. R^(δ) denotes H, an unsubstituted orsubstituted C₁-C₄₀-hydrocarbonoxy radical, an acyl radical orNR^(I)R^(II) or [NR^(I)R^(II)R^(III)]^(⊕)X^(⊖), where R^(I), R^(II) andR^(III) are identical or different and denote H or an unsubstituted orsubstituted C₁-C₃₀-hydrocarbon radical which can optionally be bound viaa group (EO)_(w), where w is an integer from 1 to 50, X^(⊖) is an anion.